Br（？）nsted酸性离子液体的合成、性质和应用研究
|
摘要
本文合成了一系列Br?nsted酸性离子液体,并以其中具代表性的14种离子液体作为溶剂和催化剂,应用到以苯腈和叔丁醇为底物的Ritter反应中。其中离子液体[NSPTEA][OTF]( N-(4-sulfonic acid) propyl triethylammonium trifluoro- methane- sulfonate)对Ritter反应表现出非常好的催化活性。这种廉价的离子液体[NSPTEA][OTF]可以通过简单的水洗和最终产物分离,大大简化了分离工艺,同时该离子液体可重复利用5次活性无明显下降。这一研究工作是首次利用Br?nsted酸性离子液体作为溶剂和催化剂进行的Ritter反应,该方法具有反应平稳,时间短,温度低,产率高,催化剂溶剂可回收,避免使用腐蚀性无机酸催化剂等优点。具有较好的潜在工业应用价值。
Br?nsted酸性离子液体([HMIM][OTF], [NSPTEA][OTF], [MPSIM][OTF], [HHDMG][OTF])作为“溶剂和催化剂”和Br?nsted酸为催化剂,IL[BMIM][BF4]为溶剂的反应体系,以2-(pyrrolidin-1-yl)benzaldehyde和苯胺为反应底物进行“tert-amino effect”关环反应,结果显示在Br?nsted酸为催化剂,IL[BMIM][BF4]为溶剂的反应体系中,以较好的收率完成了该反应,多种取代芳胺类化合物和醛类化合物被作为底物应用于该反应体系,同样取得了理想的效果。这一研究工作是首次利用离子液体作为溶剂进行的“tert-amino effect”关环反应,离子液体的使用为“tert-amino effect”关环反应提供了简单、快速、方便的新的反应体系。
Ionic liquids (ILs) that are composed entirely of ions and are liquids at ambient or far below ambient temperature, have been extensively used as a potential alternative to toxic, hazardous, flammable and highly volatile organic solvents. Indeed, their many unique and attractive physicochemical properties, including negligible vapor pressure, multiple solvation interactions with organic and inorganic compounds, excellent chemical and thermal stability, high ionic conductivity and large electrochemical window make ILs great candidates for volatile organic compounds
replacements. In addition, the physicochemical properties such as the viscosity, hydrophobicity, density, and solubility of ILs can be tuned by simply selecting different combinations of cations and anions as well as attached substituents to customize ILs for many specific demands. This is why ILs have been recognized as“designer solvents.”All these interesting combination of properties opens the road to a wide range of applications, including extraction, organic synthesis and catalysis, inorganic synthesis, separation, nanomaterial synthesis and enzymatic reactions。
Recently, Br?nsted acidic ionic liquids, which combine both advantages of solid acids (e.g. nonvolatility and easy recycle) and that of liquid acids (e.g. greater effective surface area and potential activity of liquid phase), have been designed and used as dual solvent-catalysts for Fisher esterification, alcohol dehydrodimerization pinacol/benzopinacol rearrangements, and the electrophilic substitution of indoles with aldehydes. this implementation of task specific ionic liquids (TSILs) further enhances the versatility of classical ionic liquids where both reagent and medium are coupled . The union of reagent with medium has been found to be a viable alternative approach toward modern synthetic chemistry especially when considering the growing environmental demands being placed on chemical processes.
Developments of new basic reactions and new synthetic methods are the basis for the innovation and advance of organic chemistry .Based on the research achievement of our group in room temperature ionic liquids, my thesis starts from the design and synthesis of room temperature ionic liquids, aming to develop a new synthetic strategy to provide a general and simple route to the Ritter reaction of tertiary alcohols with nitriles , investigations were also carried out on the synthetic methodology for Application of the tert-amino effect”for preparation of potentially useful aminals compounds under ionic liquid. The main content of this paper is outlined as following:
The Ritter reaction is one of the most important carbon-nitrogen bond forming reactions and is widely used to synthesize amide compounds, which are important synthetic intermediates for various pharmaceuticals and natural products. The classical Ritter reaction of tertiary and secondary alcohols with nitriles was catalyzed by strong protic acids such as concentrated sulfuric acid and some alternative acids .These procedures have advantages such as cleaner reactions, easier workup, and easier recovery and reuse of catalysts. In spite of that, it is still full of challenge to explore high catalytic activity and reusable catalysts for Ritter reaction.
In this paper, we speculate that Br?nsted acidic ionic liquids, due to their strong acidity and high polarity, maybe not only favor acid catalysis, but also favor stability of the carbocation intermediates in Ritter reaction. With the aim of finding efficient, cost-effective and reusable catalysts, we investigated the Ritter reaction of nitriles with tertiary alcohols as well as secondary alcohols in presence of Br?nsted acidic ionic liquids. To the best of our knowledge, this is the first report on the application of Br?nsted acidic ionic liquids as dual solvent-catalysts for Ritter reaction
Three classes twenty-nine kinds Br?nsted acidic ionic liquids (ILs) were synthesized and used as dual solvent-catalysts for the Ritter reaction of benzonitrile with tert-butanol. In particular, IL ([NSPTEA][OTF] )( N-(4-sulfonic acid) propyl triethylammonium trifluoromethanesulfonate) showed excellent catalytic activity for the Ritter reaction. In the presence of IL, various nitriles and tertiary alcohols as well as secondary alcohols were converted smoothly to the corresponding amides in good to excellent yields. In addition, this cost-effective ionic liquid [NSPTEA][OTF] was easily separated from the reaction mixtures by extraction with a small amount of water, and recycled five times without any significant loss in activity.
The term“tert-amino effect”has been used to describe a diverse number of reactions that proceed via intramolecular, C-C, or C-X bond-forming redox processes within conjugated systems.1 These reactions involve the functionalization of a C-H bondαto a tertiary amine nitrogen and have also been referred to as“α-cyclization of tertiary amines”. In the vast majority of cases, these reactions are promoted thermally and relatively little effort has been devoted to developing reaction approaches. To ultimately expand the scope and applicability of these intriguing transformations, it is desirable to identify new synthetic methods that would allow for milder reaction conditions as well as shorter reaction times.
In this paper, four kinds Br?nsted acidic ionic liquids (ILs) ([HMIM][OTF], [NSPTEA][OTF], [MPSIM][OTF], [HHDMG][OTF]) were synthesized and used as dual solvent-catalysts for the“tert-amino effect”ring-closure reaction of 2-(pyrrolidin-1-yl)benzaldehyde with aniline.Unluckily,none but [MPSIM][OTF], [HHDMG][OTF]) given the product of the ring-closure reaction, but the yield were not absorbing. At last we attempt Br?nsted acid-promoted syntheses of aminals from o-aminobenzaldehydes and aromatic amines that proceed in water-solubility IL[BMIM][BF4] a simple single-flask procedure.This is the first work for“tert-amino effect”ring-closure reaction in ionic liquids.
Br?nsted酸性离子液体([HMIM][OTF], [NSPTEA][OTF], [MPSIM][OTF], [HHDMG][OTF])作为“溶剂和催化剂”和Br?nsted酸为催化剂,IL[BMIM][BF4]为溶剂的反应体系,以2-(pyrrolidin-1-yl)benzaldehyde和苯胺为反应底物进行“tert-amino effect”关环反应,结果显示在Br?nsted酸为催化剂,IL[BMIM][BF4]为溶剂的反应体系中,以较好的收率完成了该反应,多种取代芳胺类化合物和醛类化合物被作为底物应用于该反应体系,同样取得了理想的效果。这一研究工作是首次利用离子液体作为溶剂进行的“tert-amino effect”关环反应,离子液体的使用为“tert-amino effect”关环反应提供了简单、快速、方便的新的反应体系。
Ionic liquids (ILs) that are composed entirely of ions and are liquids at ambient or far below ambient temperature, have been extensively used as a potential alternative to toxic, hazardous, flammable and highly volatile organic solvents. Indeed, their many unique and attractive physicochemical properties, including negligible vapor pressure, multiple solvation interactions with organic and inorganic compounds, excellent chemical and thermal stability, high ionic conductivity and large electrochemical window make ILs great candidates for volatile organic compounds
replacements. In addition, the physicochemical properties such as the viscosity, hydrophobicity, density, and solubility of ILs can be tuned by simply selecting different combinations of cations and anions as well as attached substituents to customize ILs for many specific demands. This is why ILs have been recognized as“designer solvents.”All these interesting combination of properties opens the road to a wide range of applications, including extraction, organic synthesis and catalysis, inorganic synthesis, separation, nanomaterial synthesis and enzymatic reactions。
Recently, Br?nsted acidic ionic liquids, which combine both advantages of solid acids (e.g. nonvolatility and easy recycle) and that of liquid acids (e.g. greater effective surface area and potential activity of liquid phase), have been designed and used as dual solvent-catalysts for Fisher esterification, alcohol dehydrodimerization pinacol/benzopinacol rearrangements, and the electrophilic substitution of indoles with aldehydes. this implementation of task specific ionic liquids (TSILs) further enhances the versatility of classical ionic liquids where both reagent and medium are coupled . The union of reagent with medium has been found to be a viable alternative approach toward modern synthetic chemistry especially when considering the growing environmental demands being placed on chemical processes.
Developments of new basic reactions and new synthetic methods are the basis for the innovation and advance of organic chemistry .Based on the research achievement of our group in room temperature ionic liquids, my thesis starts from the design and synthesis of room temperature ionic liquids, aming to develop a new synthetic strategy to provide a general and simple route to the Ritter reaction of tertiary alcohols with nitriles , investigations were also carried out on the synthetic methodology for Application of the tert-amino effect”for preparation of potentially useful aminals compounds under ionic liquid. The main content of this paper is outlined as following:
The Ritter reaction is one of the most important carbon-nitrogen bond forming reactions and is widely used to synthesize amide compounds, which are important synthetic intermediates for various pharmaceuticals and natural products. The classical Ritter reaction of tertiary and secondary alcohols with nitriles was catalyzed by strong protic acids such as concentrated sulfuric acid and some alternative acids .These procedures have advantages such as cleaner reactions, easier workup, and easier recovery and reuse of catalysts. In spite of that, it is still full of challenge to explore high catalytic activity and reusable catalysts for Ritter reaction.
In this paper, we speculate that Br?nsted acidic ionic liquids, due to their strong acidity and high polarity, maybe not only favor acid catalysis, but also favor stability of the carbocation intermediates in Ritter reaction. With the aim of finding efficient, cost-effective and reusable catalysts, we investigated the Ritter reaction of nitriles with tertiary alcohols as well as secondary alcohols in presence of Br?nsted acidic ionic liquids. To the best of our knowledge, this is the first report on the application of Br?nsted acidic ionic liquids as dual solvent-catalysts for Ritter reaction
Three classes twenty-nine kinds Br?nsted acidic ionic liquids (ILs) were synthesized and used as dual solvent-catalysts for the Ritter reaction of benzonitrile with tert-butanol. In particular, IL ([NSPTEA][OTF] )( N-(4-sulfonic acid) propyl triethylammonium trifluoromethanesulfonate) showed excellent catalytic activity for the Ritter reaction. In the presence of IL, various nitriles and tertiary alcohols as well as secondary alcohols were converted smoothly to the corresponding amides in good to excellent yields. In addition, this cost-effective ionic liquid [NSPTEA][OTF] was easily separated from the reaction mixtures by extraction with a small amount of water, and recycled five times without any significant loss in activity.
The term“tert-amino effect”has been used to describe a diverse number of reactions that proceed via intramolecular, C-C, or C-X bond-forming redox processes within conjugated systems.1 These reactions involve the functionalization of a C-H bondαto a tertiary amine nitrogen and have also been referred to as“α-cyclization of tertiary amines”. In the vast majority of cases, these reactions are promoted thermally and relatively little effort has been devoted to developing reaction approaches. To ultimately expand the scope and applicability of these intriguing transformations, it is desirable to identify new synthetic methods that would allow for milder reaction conditions as well as shorter reaction times.
In this paper, four kinds Br?nsted acidic ionic liquids (ILs) ([HMIM][OTF], [NSPTEA][OTF], [MPSIM][OTF], [HHDMG][OTF]) were synthesized and used as dual solvent-catalysts for the“tert-amino effect”ring-closure reaction of 2-(pyrrolidin-1-yl)benzaldehyde with aniline.Unluckily,none but [MPSIM][OTF], [HHDMG][OTF]) given the product of the ring-closure reaction, but the yield were not absorbing. At last we attempt Br?nsted acid-promoted syntheses of aminals from o-aminobenzaldehydes and aromatic amines that proceed in water-solubility IL[BMIM][BF4] a simple single-flask procedure.This is the first work for“tert-amino effect”ring-closure reaction in ionic liquids.
引文
[1] Welton, T., [J]. Chem Rev, 1999, 99: 2071.
[2] Wasserscheid, P.; Keim, W., [J]. Angew. Chem. Int. Ed., 2000, 39: 3772.
[3] Sheldon, R. A., [J].Chem. Commun., 2001, 2399.
[4] Dupont, J.; De Souza, R. F.; Suarez, P. A. Z., [J].Chem. Rev, 2002, 102: 3667.
[5] Sugden, S.; Wilkins, H. [J]. J.Chem. Soc. 1927, 1291-1298.
[6] Koch, V. R.; Miller, L. L.; Osteryoung, R. A. [J]. J.Am. Chem. Soc. 1976,5277.
[7] Wilkes, J. S.; Zaworotko, M. J. [J]. J.Chem. Soc. Chem. Com. 1992, 965.
[8] Cole, A .C; Jensen ,J .L, Ntai I et al. [J]. J.Am. Chem. Soc. 2002, 124: 5962.
[9] Bao, W. L; Wang, Z. M; Li ,Y. X. [J]. J.Org. Chem. , 2003, 68: 591.
[10] Zhao, D. B; Fei, Z. F; Geldbach, T. J, et al. [J]. J.Am. Chem. Soc. 2004, 126: 876.
[11] Leone, A. M; Weatherly, S. C; Williams, M. E, et al. [J]. J.Am. Chem. Soc. 2001, 123: 218
[12] Huang, J; Jiang, T; Gao, H. X, et al. [J]. Angew. Chem. Int. Ed. 2004, 43: 1397.
[13] Dai, L. Y; Yu, S. Y; Shan, Y. K, et al. Eur. [J]. Inorg. Chem. 2004,43:1397.
[14]刘亚强,王大伟.现代化学概论. [M]西安:陕西师范大学出版社, 2001, 185:
[15] Freemantle, [M] Chemicla & Engineering News. 2000, 78: 37.
[16] Freemantle, [M] Chemicla & Engineering News. 1999, 77: 11.
[17] Song, C.E.; Oh, C.R.; Roh, E. [J]. Chem. Commun. 2000, 18: 1743.
[18] Merrigan, T. L.; Bates, E. D.; Dorman, S. C, et al. [J]. Chem. Commun. 2000, 20: 2051.
[19] Ohno, H.; Petrotech(Tokyo). 2000, 23: 556
[20] Kitazume, T.; Kagaku Kogyo. 2000, 51: 437
[21] Hirao, M.; Sugimoto, H. Ohno, H. [J]. Electro. Chem. Soc. 2000,147: 4168.
[22] Bonhote, P.; Dias, A. P.; Papageorigiou, N. etal. [J].Inorg.Chem. 1996, 35: 1168
[23] Karodia, N.; Guise, S.; Newland, C etal. [J]. Chem. Commun. 1998, 2341:
[24] Ngo, H. I.; LeCopmpte, K.; Hargens, L etal. [J]. Therochem. Acta. 2000, 357: 97.
[25] Smith, G. P; Dworkin, A. S. [J].J.Am Chem Soc, 1989, 111: 525
[26] Wasserscheid, P; Sesing, M; Korth, W. [J].Green Chem, 2002 ,4: 134.
[27] Thomazeau, C. [J]. J Am Chem Soc, 2003, 125: 5264.
[28] Cole, A. C. [J].J Am Chem Soc, 2002, 124: 5962.
[29] Hirao, M.; Sugimoto, H. Ohno, H. [J].J. Electro. Chem. Soc. 2000, 147: 4168.
[30] Bonhote, P.; Dias, A. P.; Papageorigiou, N etal. [J].Inorg.Chem. 1996, 35: 1168.
[31] Tamar L. Greaves, Calum J. Drummond [J].Chem. Rev. 2008, 108: 206.
[32] Hua-Ping Zhu, Fan Yang, Jie Tang Ming-Yuan He [J].Green Chemistry, 2003, 5: 38.
[33] A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J.Weaver, D.C. Forbes, J.H. Davis Jr., [J]. J. Am. Chem. Soc. 2002 124: 5962–5963.
[34] J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.P. Bazureau, J. Hamelin, [J]. Catal. Commun. 2002, 3: 185–190.
[35] Hua Shi, Wenshuai Zhu, Huaming Li , Hua Liu, Ming Zhang, Yongsheng Yan, Zhigao Wang.[J]. Catalysis Communications 2010,11: 588.
[36] H.P. Nguyen, S. Znifeche, M. Baboulene, [J]. Synth. Commun. 2004, 34:2085.
[37] A. Arfan, J.P. Bazureau, [J]. Org. Proc. Res. Dev. 2005, 9: 743.
[38] H. Xing, T. Wang, Z. Zhou, Y. Dai, [J].Ind. Eng. Chem. Res. 2005, 44: 4147.
[39] T. Joseph, S. Sahoo, S.B. Halligudi, [J] J. Mol. Catal. A: Chem. 2005, 234:107.
[40] D.C. Forbes, K.J. Weaver, [J]. J. Mol. Catal. A: Chem. 2004, 214 129.
[41] J. Gui, X. Cong, D. Liu, X. Zhang, Z. Hu, Z. Sun, [J]. Catal. Commun. 2004, 5:473.
[42] Hai-Hong Wu, Fan Yang, Peng Cui, Jie Tang, Ming-Yuan He [J].Tetrahedron Letters 2004, 45: 4963.
[43] Neeraj Gupta, Sonu, Goverdhan L. Kad, Jasvinder Singh. [J] Catalysis Communications 2007,8: 1323–1328
[44] Yuanyuan Wang, Dong Jiang, Liyi Dai. [J]. Catalysis Communications 2008, 9: 2475–2480 [45 ] Smith M B, March J. Advanced Organic Chemistry [M ]. New york,Academic p ress, 2001: 1415.
[46] Zhengyin Du, Zuopeng Li , Yanlong Gu, Juan Zhang , Youquan Deng, [J].Journal of Molecular Catalysis A: Chemical 2005, 23: 80.
[47] M. Arend, B. Westermann, N. Risch, [J]. Angew. Chem., Int. Ed. Engl. 1998, 37: 1044.
[48] B. List, P. Pojarliev, W.T. Biller, H.J. Martin, [J]. J. Am. Chem. Soc. 2002, 124: 827.
[49] B. List, [J]. J. Am. Chem. Soc. 2000, 122: 9336.
[50] R.O. Duthaler, [J]. Angew. Chem. Int. Ed. 2003, 42: 975.
[51] K. Mogilaiah, G. Kankaiah, Indian [J].J. Heterocycl. Chem. 2002, 11: 283.
[52] K. Manabe, Y. Mori, S. Kobayashi, [J]. Tetrahedron 2001, 57: 2537.
[53] S. Kobayashi, T. Hamada, K. Manabe, [J].J. Am. Chem. Soc. 2002 124: 5640.
[54] P. Desai, K. Schildknegt, K.A. Agrios, C. Mossman, G.L. Milligan, J. Aube, [J]. J. Am. Chem. Soc. 2000, 122: 7226.
[55] Suman Sahoo, Trissa Joseph , S.B. Halligudi Journal of Molecular Catalysis A: Chemical 2006, 244: 179.
[56] Fang Dong , Fei Zhenghao , Liu Zuliang [J]. Catalysis Communications 2009, 10: 1267.
[57] E. Arundale, L.A. Mikeska, [J].Chem. Rev. 1952, 51: 505.
[58] H.M.S. Kumar, N.A. Qazi, S. Shafi, V.N. Kumar, [J]. Tetrahedron Lett. 2005, 46: 7205.
[59] J.S. Yadav, B.V. Reddy, G. Bhaishya, [J]. Green Chem. 2003, 264.
[60] K.-P. Chan, T.-P. Loh, [J]. Tetrahedron Lett. 2004, 45: 8387.
[61] M. Dziedzic, G. Lipner, B. Furman, [J]. Tetrahedron Lett. 46 2005, 46: 6861.
[62] Y. Du, F. Tian, [J].Catal. Commun. 2007, 8: 2012.
[63] G. Li, Y. Gu, Y. Ding, H. Zhang, J. Wang, Q. Gao, L. Yan, J. Suo, [J].J. Mol. Catal.A: Chem. 2004, 218: 147.
[64] M.K. Vadav, R.V. Jasra, [J].Catal. Commun. 2006, 7 891.
[65] H. Wang, Z. Liu, C. Sun, G. Wang, [J]. Catal. Today 2004, 425: 93.
[66] B. Sreedhar, V. Swapna, C. Sridhar, D. Saileela, A. Sunitha, [J].Synth. Commun. 2005, 35: 1177.
[67] H.J. Prins, Chem. Week 1919, 16: 1072.
[68] Dong Fang , Chang-mei Jiao, Hua-bin Zhang, Bao-hua Ji. [J]. Journal of Industrial and Engineering Chemistry 2010,16: 233.
[69] Y. Xia, Z.Y. Yang, K.F. Bastow, Y. Nakanishi, K.H. Lee.[J]. Bioorg. Med. Chem. Lett. 2000, 10: 699.
[70] H.K. Hsieh, L.T. Tsao, J.P. Wang. J. Pharm. Pharmacol. 2000, 52: 163.
[71] J. Rojas, M. Paya, J.N. Dominguez, M. Luisa Ferrandiz. [J].Bioorg. Med. Chem. Lett. 2002, 12: 1951.
[72] M. Satyanarayana, P. Tiwari, B.K. Tripathi, A.K. Srivastava, R. Pratap. [J]. Bioorg. Med. Chem. 2004, 12: 883.
[73] T. Narender, K.P. Reddy. [J]. Tetrahedron Lett. 2007, 48: 3177.
[74] N.O. Calloway, L.D. Green. J. Am. Chem. Soc. 59 1937, 59: 809.
[75] L. Mazza, A. Guaram. [J].Synthesis. 1980. 41.
[76] N. Iranpoor, F. Kazemi, [J]. Tetrahedron 1998, 54: 9475.
[77] T. Szell, I. Sohar, Can. [J].J. Chem. 1969, 47: 1254.
[78] M.T. Climent, A. Corma, S. Iborra. J. Primo, [J].J. Catal. 1995, 151: 60.
[79] M.T. Drexler, J. Amiridis. [J].J. Catal. 2003, 214 136.
[80] B.M. Choudary, K.V.S. Ranganath, J. Yadav, M.L. Kantam. [J].Tetrahedron Lett. 2005, 46: 1369.
[81] S. Saravanamurugan, M. Palanichamy, B. Arabindo, V. Murugesan. [J].J. Mol. Catal.A: Chem. 2004, 218: 101.
[82] J.B. Daskiewicz, G. Comte, D. Barron, A.D. Pietro, F. Thomasson.[J].Tetrahedron Lett. 1999, 40: 7095.
[83] S. Sebti, A. Solhy, A. Smahi, A. Kossir, H. Oumimoun. [J].Catal. Commun. 2002, 3: 335.
[84] X. Wang, S. Cheng. [J]. Catal. Commun. 2006, 7: 689.
[85] Fang Dong , Cheng Jian, Fei Zhenghao, Gong Kai Liu Zuliang. [J].Catalysis Communications 2008, 9: 1924.
[86] H.V. Pechmann, C. Duisberg, Ber. 1883, 16: 2119.
[87] H.V. Pechmann, C. Duisberg, Ber. 1884, 17: 929.
[88] M. Bulut, C. Erk, Dyes Pigments 1996, 30: 99.
[89] A. Robertson, W.F. Sandrock, C.B. Henery. [J].J. Chem. Soc. 1931, 2426.
[90] Vasundhara Singh, Sukhbir Kaur, Varinder Sapehiyia, J. Singh, G.L. Kad [J].Catalysis Communications 2005, 6: 57.
[91] Satoshi Kitaoka, Kaoru Nobuoka , Yuichi Ishikawa. [J].Tetrahedron 2005, 61: 7678.
[92] Satoshi Kitaoka, Kaoru Nobuoka , Yuichi Ishikawa Chem.Commun.2004,1902.
[93] Fang Dong , Gong Kai , Fei Zhenghao , Zhou Xinli , Liu Zuliang .[J].Catalysis Communications 2008, 9: 317.
[94] Taterao M. Potewar, Shafi A. Siddiqui, Rajgopal J. Lahoti , Kumar V. Srinivasan. [J].Tetrahedron Letters 2007, 48: 1721.
[95] Dong Fang, Qun-Rong Shi, Jian Cheng, Kai Gong, Zu-Liang Liu . [J].Applied Catalysis A: General 2008, 345: 158.
[96] Du, Y.; Tian, F. [J]. J. Chem. Res. 2006, 8: 486.
[97] Siddiqui, S. A.; Potewar, T. M.; Lahoti, R. J.; Srinivasan, K. V. [J].Synthesis 2006, 17:2849.
[98] Karthikeyan, G.; Perumal, P. T. Can. [J].J. Chem. 2005, 83:1746.
[99] Diels, O.; Alder, K. Liebigs Ann. 1928, 460, 95.
[100] Rideout, D. C.; Breslow, R. J. [J]. J. Am. Chem. Soc. 1980, 102: 7816.
[101] Diego-Castro, M. J.; Hailes, H. C. [J]. Tetrahedron Lett. 1998, 39: 2211.
[102] Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. [J]. Synlett 1995, 565.
[103] Imperato, G.; Eibler, E.; Niedermaier, J.; Ko¨nig, B. [J]. Chem. Commun. 2005, 1170.
[104] Janus, E.; Goc-Maciejewska, I.; Lozynski, M.; Pernak, J. [J].Tetrahedron Lett. 2006, 47: 4079
[105] Duan, Z. Y.; Gu, Y. L.; Zhang, J.; Zhu, L. Y.; Deng, Y. Q. [J].J. Mol. Catal., A: Chem. 2006, 250: 163.
[106] Gui, J. Z.; Ban, H. Y.; Cong, X. H.; Zhang, X. T.; Hu, Z. D.; Sun, Z. L. [J].J. Mol. Catal., A: Chem. 2005, 225: 27.
[107] Olah, G. A.; Mathew, T.; Goeppert, A.; Torok, B.; Bucsi, I.; Li, X. Y.; Wang, Q.; Marinez, E. R.; Batamack, P.; Aniszfeld, R.; Prakash,G. K. S. [J].J. Am. Chem. Soc. 2005, 127: 5964.
[108] Zhang, P. P.; Du, J. Y.; Yang, F.; Zou, G.; Tang, [J]. J. Chin. J. Chem. 2005, 23: 581.
[109] Wang, H.; Cui, P.; Zou, G.; Yang, F.; Tang, J. [J]. Tetrahedron 2006, 62: 3985.
[110] Duan, Z. Y.; Gu, Y. L.; Deng, Y. Q. [J].Synth. Commun. 2005, 35: 1939.
[111] Moreau, C.; Finiels, A.; Vanoye, L. [J].J. Mol. Catal., A: Chem. 2006, 253: 165.
[112] Lansalot-Matras, C.; Moreau, C. [J].Catal. Commun. 2003, 4: 517.
[113] Biginelli, P. Aldehyde–urea derivatives of aceto- and oxaloacetic acids. Gazz. Chim. Ital. 1893, 23, 360.
[114] Shaabani, A.; Rahmati, A. [J].Catal. Lett. 2005, 100: 177.
[115] Zheng, R.; Wang, X.; Xu, H.; Du, J. [J]. Synth. Commun. 2006, 36: 1503.
[116] Palimkar, S. S.; Siddiqui, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. [J]. J. Org. Chem. 2003, 68: 9371.
[117] Weng, J. Y.; Wang, C. M.; Li, H. R.; Wang, Y. [J].Green Chem. 2006, 8:96.
[118] A. Davoodnia, M. Bakavoli, R. Moloudi, M. Khashi, N. Tavakoli-Hoseini [J]. Chinese Chemical Letters 2010, 21: 1.
[119] Abdol R. Hajipour, Yosof Ghayeb, Nafisehsadat Sheikhan, Arnold E. Ruoho. [J].Tetrahedron Letters 2009, 50 5649.
[120] Elise-Marie Dukuzeyezu Herve′Lefebvre, Martine Tessier, Alain Fradet. [J]. Polymer 2010, 51 1218.
[121] Rogers, R. D.; Seddon, K. R. [J].Science 2003, 302: 792
[122] BASF-BASIL process, 2007; http://www2.basf.de/en/intermed/nbd/products/ ionic_liquids
[1] Cole A.C., Jensen J.L., Ntai I, etal. [J].J. Am .Chem. Soc., 2002, 124: 5962.
[2]张所波,丁孟贤,高连勋. [J].有机化学,2002,22(3):159.
[3] Hua-Ping Zhu, Fan Yang. [J]. Green Chemistry, 2003, 5: 38>
[4] Brunelle,D.J.;scotia,N.Y. US Pat, 5229482 (1993)
[5] Brunelle D.J.;scotia,N.Y.US Pat.5229482 (1993).
[6] Huang J.; Jiang T.; Gao H.; Han B.; Liu Z.; Wu W.; Chang Y.; Zhao G., [J].Angew. Chem. Int. Ed, 2004, 43: 1397.
[7] Brunelle D. J.; scotia N. Y., US Pat, 5082968 (1992).
[8] Barton D. H.; Elliott J. D.; Géro S. D. [J]. J. Chem. Soc. Perkin. Trans. I 1982, 2085
[9] Isobe T.; Fukuda K.; Ishikawa T. [J].Tetrahedron: Asymmetry, 1998, 9: 1729
[10] Isobe T.; Fukuda K.; Ishikawa T., [J].J. Org. Chem. 2000, 65: 7770.
[11] Schlama T.; Gouverneur V.; Valleix A.; Greiner A.; Toupet L.; Mioskowlki C.; [J].J. Org. Chem. 1997, 62: 4200.
[12] Hua-Ping Zhu, Fan Yang, Jie Tang Ming-Yuan He [J]. Green Chemistry, 2003, 5: 38.
[13] A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J.Weaver, D.C. Forbes, J.H. Davis Jr. [J]. J. Am. Chem. Soc. 2002, 124: 5962.
[1] Ritter, J. J.; Minieri, P. P. [J]. J. Am. Chem. Soc. 1948, 70: 4045.
[2] Benson, F. R; Ritter, J. J. [J]. J. Am. Chem. Soc. 1949, 71: 4128.
[3] Reddy, K. L. [J]. Tetrahedron Lett. 2003, 44: 1453.
[4] Olah, G. A.; Yamato, T.; Iyer, P. S.; etal. [J]. Mater. Chem. Phys. 1987, 17:21.
[5] Polshettiwar, V.; Varma, R. S. [J]. Tetrahedron Lett. 2008, 49: 2661.
[6] Martinez, A. G.; Alvarez, R. M.; Vilar, E. T.; etal. [J]. Tetrahedron Lett. 1989, 30: 581.
[7] Firouzabadi, H.; Sardarian, A. R.; Badparva, H. [J]. Synthetic Commun. 1994, 601.
[8] Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. [J]. J . Org . Chem. 1995, 60: 2670.
[9] Mukhopadhyay, M.; Iqbal, J. [J].J .Org .Chem.1997, 62: 1843.
[10] Sharghi, H.; Niknam, K. [J]. Iran J. Chem. Chem. Eng. 1999, 18: 36.
[11] Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. [J].Tetrahedron .2000, 56:3077.
[12] Chen, X.; Okuhara, T. [J]. J. Catal. 2002, 207: 194.
[13] Salehi, P.; Motlagh, A. P. [J]. Synthetic. Commun. 2000, 671.
[14] Lakourag, M. M.; Movassagh, B.; Fasihi, [J]. Synthetic. Commun. 2000, 821.
[15] Okuhara, T.; Chen, X.; Matsuda, H. [J]. Appl. Catal. A: Gen. 2000, 200: 109.
[16] Callens, E.; Burton, A. J.; Barrett, A. G. M. [J]. Tetrahedron Lett. 2006, 47: 8699.
[17] Tamaddon, F.; Khoobi, M.; Keshavarz, E. [J]. Tetrahedron Lett. 2007, 48: 3643.
[18] Firouzabadi, H.; Iranpoor, N.; Khoshnood, A. [J]. Catal.Commun. 2008, 9: 529.
[19] Yadav, J. S.; Reddy, B. V. S.; Pandurangam, T.; etal. [J]. Catal.Commun. 2008, 9: 1297.
[20] Bruno Anxionnat, [J]. [J]. Tetrahedron Letters, 2009, 02: 1
[21] Clément Cazorla, Estelle Métay, Bruno Andrioletti, Marc Lemaire. [J].Tetrahedron Letters 2009, 50: 6855.
[22] (a) Maillard, M. C.; Hom, R. K.; Benson, T. E.; Moon, J. B.; Mamo, S.; Bienkowski, M.; Tomasselli, A. G.; Woods, D. D.; Prince, D. B.; Paddock, D. J.; Emmons, T. L.;Tucker, J. A.; Dappen, M. S.; Brogley, L.; Thorsett, E. D.; Jewett, N.; Sinha, S.;John, V. [J].J. Med. Chem. 2007, 50: 776. (b) Liao, Y. F.; Wang, B.-J.; Hsu, W. M.; Lee,H.; Liao, C. Y.; Wu, S. Y.; Cheng, H. T.; Hu, M. K. Mol. [J]. Pharmacol. 2007, 71: 588.(c) Bakshi, P.; Wolfe, M. S. [J].J. Med. Chem. 2004, 47:6485.
[23] (a) Beaulieu, P. L.; Wernic, D.; Abraham, A.; Anderson, P. C.; Bogri, T.; Bousquet,Y.; Croteau, G.; Guse, I.; Lamarre, D.; Liard, F.; Paris, W.; Thibeault, D. [J]. J. Med.Chem. 1997, 40: 2164. (b) Kempf, D. J.; Codavoci, L.; Wang, X. C.; Kohlbrenner,W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.;Sham, H. L.; Green, B. E.; Betebenner, D. A.; Erickson, J.; Norbeck, D. W. [J]. J. Med.Chem. 1993, 36: 320.(c) Medou, M.; Priem, G.; Rocheblave, L.; Pepe, G.; Meyer,M.; Chermann, J. C.; Kraus, J. L. Eur. [J]. J. Med. Chem. 1999, 34: 625.
[24] (a) Lee, C. E.; Kick, E. K.; Ellman, J. A. [J].J. Am. Chem. Soc. 1998, 120: 9735; (b) Kick,E. K.; Roe, D. C.; Geoffrey Skillman, A.; Liu, G.; Ewing, T. J. A.; Sun, Y.; Kuntz, I. D.;Ellman, [J]. J. A. Chem. Biol. 1997, 4: 297.
[25] Haque, T. S.; Geoffrey Skillman, A.; Lee, C. E.; Habashita, H.; Gluzman, I. Y.;Ewing, T. J. A.; Goldberg, D. E.; Kuntz, I. D.; Ellman. [J].J. A. J. Med. Chem. 1999, 42: 1428.
[26] Concellón, J. M.; Suárez, J. R.; Del Solar, V. [J]. J. Org. Chem. 2005, 70: 7447.
[27] Mickael Dos Santos, Benoit Crousse , Danièle Bonnet-Delpon [J].Tetrahedron Letters 2009, 50: 857.
[28] Kristof Van Emelen,? Tom De Wit, Georges J. Hoornaert, and Frans Compernolle [J]. Org. Lett., 2000, 2: 3083.
[29] Kristof Van Emelen, Tom De Wit, Georges J. Hoornaert, Frans Compernolle , [J]. Tetrahedron 2002, 58: 4225.
[30] Jose′M. Concello′N, Estela Riego, Jose′Ramo′n Sua′rez, Santiago Garc ?′a -Granda, M. Rosario D?′az [J]. Org. Lett., , 2004 , 6: 4499.
[31] J.S. Yadav , [J]. Tetrahedron 2008, 64: 3025.
[32] J. S. Yadav, [J].Tetrahedron Letters 2007, 48: 4903.
[33] Vijay Nair, Roshini Rajan, Nigam P. Rath. [J]. Org. Lett. 2002, 4: 1575.
[34] Oleg L. Epstein , Tomislav Rovis. [J]. J. Am. Chem. soc. 2006,128: 16480.
[35] Gowravaram Sabitha , M. Bhikshapathi , Sambit Nayak , J. S. Yadav , R. Ravi , A. C. Kunwar [J]. Tetrahedron Letters 2008, 49: 5727.
[36] Cole, A. C.; Jensen, J. L.; Ntai, L.; etal. [J].J. Am. Chem. Soc. 2002, 124: 5962.
[37] Zhu, H. P.; Yang, F.; Tang, J.; He, M.Y. [J]. Green.Chem. 2003, 5: 38.
[38] Xing, H.; Wang, T.; Zhou, Z.; etal. [J]. Ind. Eng. Chem. Res. 2005, 44: 4147.
[39] Fang, D.; Zhou, X.; Ye, Z.; Liu, Z. L. [J]. Ind. Eng. Chem. Res. 2006, 45: 7982.
[40] Du, D.; Ji, S.; Jang, Z. [J]. Synlett. 2005, 959.
[41] Callens, E.; Burton, A. J.; Barrett, A. G. M. [J].Tetrahedron Lett. 2006, 47: 8699.
[42] Firouzabadi, H.; Iranpoor, N.; Khoshnood, A.Catal.Commun. 2008, 9, 529.
[1] J. Pinnow and G. Pistor, Ber. Deut. Chem. Ges., 1894, 27: 602.
[2] J. Pinnow, Ber. Deut. Chem. Ges. 1895, 28: 3039
[3] J. Pinnow, Ber. Deut. Chem. Ges. 1897, 30: 3119.
[4] J. Pinnow, Ber. Deut. Chem. Ges. 1898, 31: 2982.
[5] J. Pinnow, Ber. Deut. Chem. Ges. 1899, 32: 1666.
[6] A. Schuster and J. Pinnow, Ber. Deut. Chem. Ges. 1896, 29: 1053.
[7] METH-COHN 0, [J].Advances in Heterocyclic Chemistry, 1972,14:211.
[8] V, PE工NADOR C, [J].Synthesis, 1993, 152.
[9] OJEA V, [J].Synlett, 1995, 622.
[10] OJEA V, [J].Tetrahedron, 1998, 54: 927.
[11] CHANTEGREL B, DESHAYES C, [J].Tetrahedron Letters, 1995, 36:7859.
[12] TVERDOKHLEBOV A V, GORLLYA A P etal. [J].Tetrahedron, 2006, 62: 9146.
[13] KAVA N, HALASZ-DAJKA B,VO-THANH G,etal. [J].Tetrahedron,2005 61: 9052.
[14] SCHWART A, BEKE G, KOVARI Z, etal. [J]. Journal of Molecular Structure: 2000, 528: 49.
[15] Petra Dunkel , Gyorgy Turos, Attila Benyei, Krisztina Ludanyi, Peter Matyus. [J]. Tetrahedron 2010, 66: 2331.
[16] O. V. Ryabtsova, A. F. Pozharskii, A. V. Degtyarev and V. A. Ozeryanskii, Mendeleev Commun., 2006, 313.
[17] (a) Meth-Cohn, O.; Naqui, M. A. [J]. Chem. Commun. 1967, 1157..(b) Grantham, R. K.; Meth-Cohn, O. [J]. Chem. Commun. 1968, 500. (c) Grantham, R. K.; Meth-Cohn, O.; Naqui, M. A. [J]. J. Chem. Soc., C 1969, 1438. (d) Grantham, R. K.; Meth-Cohn, O. [J]. J. Chem. Soc., C 1969, 1444.
[18] Zhang, C.; De, C. K.; Mal, R.; Seidel, D. [J]. J. Am. Chem. Soc. 2008, 130: 416.
[19] Verboom, W.; Hamzink, M. R. J.; Reinhoudt, D. N.; Visser, R. [J]. Tetrahedron Lett. 1984, 25: 4309.
[20] Chen Zhang; Sandip Murarka; Daniel Seidel. [J]. J. Org. Chem. 2009, 74: 419.
[2] Wasserscheid, P.; Keim, W., [J]. Angew. Chem. Int. Ed., 2000, 39: 3772.
[3] Sheldon, R. A., [J].Chem. Commun., 2001, 2399.
[4] Dupont, J.; De Souza, R. F.; Suarez, P. A. Z., [J].Chem. Rev, 2002, 102: 3667.
[5] Sugden, S.; Wilkins, H. [J]. J.Chem. Soc. 1927, 1291-1298.
[6] Koch, V. R.; Miller, L. L.; Osteryoung, R. A. [J]. J.Am. Chem. Soc. 1976,5277.
[7] Wilkes, J. S.; Zaworotko, M. J. [J]. J.Chem. Soc. Chem. Com. 1992, 965.
[8] Cole, A .C; Jensen ,J .L, Ntai I et al. [J]. J.Am. Chem. Soc. 2002, 124: 5962.
[9] Bao, W. L; Wang, Z. M; Li ,Y. X. [J]. J.Org. Chem. , 2003, 68: 591.
[10] Zhao, D. B; Fei, Z. F; Geldbach, T. J, et al. [J]. J.Am. Chem. Soc. 2004, 126: 876.
[11] Leone, A. M; Weatherly, S. C; Williams, M. E, et al. [J]. J.Am. Chem. Soc. 2001, 123: 218
[12] Huang, J; Jiang, T; Gao, H. X, et al. [J]. Angew. Chem. Int. Ed. 2004, 43: 1397.
[13] Dai, L. Y; Yu, S. Y; Shan, Y. K, et al. Eur. [J]. Inorg. Chem. 2004,43:1397.
[14]刘亚强,王大伟.现代化学概论. [M]西安:陕西师范大学出版社, 2001, 185:
[15] Freemantle, [M] Chemicla & Engineering News. 2000, 78: 37.
[16] Freemantle, [M] Chemicla & Engineering News. 1999, 77: 11.
[17] Song, C.E.; Oh, C.R.; Roh, E. [J]. Chem. Commun. 2000, 18: 1743.
[18] Merrigan, T. L.; Bates, E. D.; Dorman, S. C, et al. [J]. Chem. Commun. 2000, 20: 2051.
[19] Ohno, H.; Petrotech(Tokyo). 2000, 23: 556
[20] Kitazume, T.; Kagaku Kogyo. 2000, 51: 437
[21] Hirao, M.; Sugimoto, H. Ohno, H. [J]. Electro. Chem. Soc. 2000,147: 4168.
[22] Bonhote, P.; Dias, A. P.; Papageorigiou, N. etal. [J].Inorg.Chem. 1996, 35: 1168
[23] Karodia, N.; Guise, S.; Newland, C etal. [J]. Chem. Commun. 1998, 2341:
[24] Ngo, H. I.; LeCopmpte, K.; Hargens, L etal. [J]. Therochem. Acta. 2000, 357: 97.
[25] Smith, G. P; Dworkin, A. S. [J].J.Am Chem Soc, 1989, 111: 525
[26] Wasserscheid, P; Sesing, M; Korth, W. [J].Green Chem, 2002 ,4: 134.
[27] Thomazeau, C. [J]. J Am Chem Soc, 2003, 125: 5264.
[28] Cole, A. C. [J].J Am Chem Soc, 2002, 124: 5962.
[29] Hirao, M.; Sugimoto, H. Ohno, H. [J].J. Electro. Chem. Soc. 2000, 147: 4168.
[30] Bonhote, P.; Dias, A. P.; Papageorigiou, N etal. [J].Inorg.Chem. 1996, 35: 1168.
[31] Tamar L. Greaves, Calum J. Drummond [J].Chem. Rev. 2008, 108: 206.
[32] Hua-Ping Zhu, Fan Yang, Jie Tang Ming-Yuan He [J].Green Chemistry, 2003, 5: 38.
[33] A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J.Weaver, D.C. Forbes, J.H. Davis Jr., [J]. J. Am. Chem. Soc. 2002 124: 5962–5963.
[34] J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.P. Bazureau, J. Hamelin, [J]. Catal. Commun. 2002, 3: 185–190.
[35] Hua Shi, Wenshuai Zhu, Huaming Li , Hua Liu, Ming Zhang, Yongsheng Yan, Zhigao Wang.[J]. Catalysis Communications 2010,11: 588.
[36] H.P. Nguyen, S. Znifeche, M. Baboulene, [J]. Synth. Commun. 2004, 34:2085.
[37] A. Arfan, J.P. Bazureau, [J]. Org. Proc. Res. Dev. 2005, 9: 743.
[38] H. Xing, T. Wang, Z. Zhou, Y. Dai, [J].Ind. Eng. Chem. Res. 2005, 44: 4147.
[39] T. Joseph, S. Sahoo, S.B. Halligudi, [J] J. Mol. Catal. A: Chem. 2005, 234:107.
[40] D.C. Forbes, K.J. Weaver, [J]. J. Mol. Catal. A: Chem. 2004, 214 129.
[41] J. Gui, X. Cong, D. Liu, X. Zhang, Z. Hu, Z. Sun, [J]. Catal. Commun. 2004, 5:473.
[42] Hai-Hong Wu, Fan Yang, Peng Cui, Jie Tang, Ming-Yuan He [J].Tetrahedron Letters 2004, 45: 4963.
[43] Neeraj Gupta, Sonu, Goverdhan L. Kad, Jasvinder Singh. [J] Catalysis Communications 2007,8: 1323–1328
[44] Yuanyuan Wang, Dong Jiang, Liyi Dai. [J]. Catalysis Communications 2008, 9: 2475–2480 [45 ] Smith M B, March J. Advanced Organic Chemistry [M ]. New york,Academic p ress, 2001: 1415.
[46] Zhengyin Du, Zuopeng Li , Yanlong Gu, Juan Zhang , Youquan Deng, [J].Journal of Molecular Catalysis A: Chemical 2005, 23: 80.
[47] M. Arend, B. Westermann, N. Risch, [J]. Angew. Chem., Int. Ed. Engl. 1998, 37: 1044.
[48] B. List, P. Pojarliev, W.T. Biller, H.J. Martin, [J]. J. Am. Chem. Soc. 2002, 124: 827.
[49] B. List, [J]. J. Am. Chem. Soc. 2000, 122: 9336.
[50] R.O. Duthaler, [J]. Angew. Chem. Int. Ed. 2003, 42: 975.
[51] K. Mogilaiah, G. Kankaiah, Indian [J].J. Heterocycl. Chem. 2002, 11: 283.
[52] K. Manabe, Y. Mori, S. Kobayashi, [J]. Tetrahedron 2001, 57: 2537.
[53] S. Kobayashi, T. Hamada, K. Manabe, [J].J. Am. Chem. Soc. 2002 124: 5640.
[54] P. Desai, K. Schildknegt, K.A. Agrios, C. Mossman, G.L. Milligan, J. Aube, [J]. J. Am. Chem. Soc. 2000, 122: 7226.
[55] Suman Sahoo, Trissa Joseph , S.B. Halligudi Journal of Molecular Catalysis A: Chemical 2006, 244: 179.
[56] Fang Dong , Fei Zhenghao , Liu Zuliang [J]. Catalysis Communications 2009, 10: 1267.
[57] E. Arundale, L.A. Mikeska, [J].Chem. Rev. 1952, 51: 505.
[58] H.M.S. Kumar, N.A. Qazi, S. Shafi, V.N. Kumar, [J]. Tetrahedron Lett. 2005, 46: 7205.
[59] J.S. Yadav, B.V. Reddy, G. Bhaishya, [J]. Green Chem. 2003, 264.
[60] K.-P. Chan, T.-P. Loh, [J]. Tetrahedron Lett. 2004, 45: 8387.
[61] M. Dziedzic, G. Lipner, B. Furman, [J]. Tetrahedron Lett. 46 2005, 46: 6861.
[62] Y. Du, F. Tian, [J].Catal. Commun. 2007, 8: 2012.
[63] G. Li, Y. Gu, Y. Ding, H. Zhang, J. Wang, Q. Gao, L. Yan, J. Suo, [J].J. Mol. Catal.A: Chem. 2004, 218: 147.
[64] M.K. Vadav, R.V. Jasra, [J].Catal. Commun. 2006, 7 891.
[65] H. Wang, Z. Liu, C. Sun, G. Wang, [J]. Catal. Today 2004, 425: 93.
[66] B. Sreedhar, V. Swapna, C. Sridhar, D. Saileela, A. Sunitha, [J].Synth. Commun. 2005, 35: 1177.
[67] H.J. Prins, Chem. Week 1919, 16: 1072.
[68] Dong Fang , Chang-mei Jiao, Hua-bin Zhang, Bao-hua Ji. [J]. Journal of Industrial and Engineering Chemistry 2010,16: 233.
[69] Y. Xia, Z.Y. Yang, K.F. Bastow, Y. Nakanishi, K.H. Lee.[J]. Bioorg. Med. Chem. Lett. 2000, 10: 699.
[70] H.K. Hsieh, L.T. Tsao, J.P. Wang. J. Pharm. Pharmacol. 2000, 52: 163.
[71] J. Rojas, M. Paya, J.N. Dominguez, M. Luisa Ferrandiz. [J].Bioorg. Med. Chem. Lett. 2002, 12: 1951.
[72] M. Satyanarayana, P. Tiwari, B.K. Tripathi, A.K. Srivastava, R. Pratap. [J]. Bioorg. Med. Chem. 2004, 12: 883.
[73] T. Narender, K.P. Reddy. [J]. Tetrahedron Lett. 2007, 48: 3177.
[74] N.O. Calloway, L.D. Green. J. Am. Chem. Soc. 59 1937, 59: 809.
[75] L. Mazza, A. Guaram. [J].Synthesis. 1980. 41.
[76] N. Iranpoor, F. Kazemi, [J]. Tetrahedron 1998, 54: 9475.
[77] T. Szell, I. Sohar, Can. [J].J. Chem. 1969, 47: 1254.
[78] M.T. Climent, A. Corma, S. Iborra. J. Primo, [J].J. Catal. 1995, 151: 60.
[79] M.T. Drexler, J. Amiridis. [J].J. Catal. 2003, 214 136.
[80] B.M. Choudary, K.V.S. Ranganath, J. Yadav, M.L. Kantam. [J].Tetrahedron Lett. 2005, 46: 1369.
[81] S. Saravanamurugan, M. Palanichamy, B. Arabindo, V. Murugesan. [J].J. Mol. Catal.A: Chem. 2004, 218: 101.
[82] J.B. Daskiewicz, G. Comte, D. Barron, A.D. Pietro, F. Thomasson.[J].Tetrahedron Lett. 1999, 40: 7095.
[83] S. Sebti, A. Solhy, A. Smahi, A. Kossir, H. Oumimoun. [J].Catal. Commun. 2002, 3: 335.
[84] X. Wang, S. Cheng. [J]. Catal. Commun. 2006, 7: 689.
[85] Fang Dong , Cheng Jian, Fei Zhenghao, Gong Kai Liu Zuliang. [J].Catalysis Communications 2008, 9: 1924.
[86] H.V. Pechmann, C. Duisberg, Ber. 1883, 16: 2119.
[87] H.V. Pechmann, C. Duisberg, Ber. 1884, 17: 929.
[88] M. Bulut, C. Erk, Dyes Pigments 1996, 30: 99.
[89] A. Robertson, W.F. Sandrock, C.B. Henery. [J].J. Chem. Soc. 1931, 2426.
[90] Vasundhara Singh, Sukhbir Kaur, Varinder Sapehiyia, J. Singh, G.L. Kad [J].Catalysis Communications 2005, 6: 57.
[91] Satoshi Kitaoka, Kaoru Nobuoka , Yuichi Ishikawa. [J].Tetrahedron 2005, 61: 7678.
[92] Satoshi Kitaoka, Kaoru Nobuoka , Yuichi Ishikawa Chem.Commun.2004,1902.
[93] Fang Dong , Gong Kai , Fei Zhenghao , Zhou Xinli , Liu Zuliang .[J].Catalysis Communications 2008, 9: 317.
[94] Taterao M. Potewar, Shafi A. Siddiqui, Rajgopal J. Lahoti , Kumar V. Srinivasan. [J].Tetrahedron Letters 2007, 48: 1721.
[95] Dong Fang, Qun-Rong Shi, Jian Cheng, Kai Gong, Zu-Liang Liu . [J].Applied Catalysis A: General 2008, 345: 158.
[96] Du, Y.; Tian, F. [J]. J. Chem. Res. 2006, 8: 486.
[97] Siddiqui, S. A.; Potewar, T. M.; Lahoti, R. J.; Srinivasan, K. V. [J].Synthesis 2006, 17:2849.
[98] Karthikeyan, G.; Perumal, P. T. Can. [J].J. Chem. 2005, 83:1746.
[99] Diels, O.; Alder, K. Liebigs Ann. 1928, 460, 95.
[100] Rideout, D. C.; Breslow, R. J. [J]. J. Am. Chem. Soc. 1980, 102: 7816.
[101] Diego-Castro, M. J.; Hailes, H. C. [J]. Tetrahedron Lett. 1998, 39: 2211.
[102] Handy, S. T.; Grieco, P. A.; Mineur, C.; Ghosez, L. [J]. Synlett 1995, 565.
[103] Imperato, G.; Eibler, E.; Niedermaier, J.; Ko¨nig, B. [J]. Chem. Commun. 2005, 1170.
[104] Janus, E.; Goc-Maciejewska, I.; Lozynski, M.; Pernak, J. [J].Tetrahedron Lett. 2006, 47: 4079
[105] Duan, Z. Y.; Gu, Y. L.; Zhang, J.; Zhu, L. Y.; Deng, Y. Q. [J].J. Mol. Catal., A: Chem. 2006, 250: 163.
[106] Gui, J. Z.; Ban, H. Y.; Cong, X. H.; Zhang, X. T.; Hu, Z. D.; Sun, Z. L. [J].J. Mol. Catal., A: Chem. 2005, 225: 27.
[107] Olah, G. A.; Mathew, T.; Goeppert, A.; Torok, B.; Bucsi, I.; Li, X. Y.; Wang, Q.; Marinez, E. R.; Batamack, P.; Aniszfeld, R.; Prakash,G. K. S. [J].J. Am. Chem. Soc. 2005, 127: 5964.
[108] Zhang, P. P.; Du, J. Y.; Yang, F.; Zou, G.; Tang, [J]. J. Chin. J. Chem. 2005, 23: 581.
[109] Wang, H.; Cui, P.; Zou, G.; Yang, F.; Tang, J. [J]. Tetrahedron 2006, 62: 3985.
[110] Duan, Z. Y.; Gu, Y. L.; Deng, Y. Q. [J].Synth. Commun. 2005, 35: 1939.
[111] Moreau, C.; Finiels, A.; Vanoye, L. [J].J. Mol. Catal., A: Chem. 2006, 253: 165.
[112] Lansalot-Matras, C.; Moreau, C. [J].Catal. Commun. 2003, 4: 517.
[113] Biginelli, P. Aldehyde–urea derivatives of aceto- and oxaloacetic acids. Gazz. Chim. Ital. 1893, 23, 360.
[114] Shaabani, A.; Rahmati, A. [J].Catal. Lett. 2005, 100: 177.
[115] Zheng, R.; Wang, X.; Xu, H.; Du, J. [J]. Synth. Commun. 2006, 36: 1503.
[116] Palimkar, S. S.; Siddiqui, S. S.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. [J]. J. Org. Chem. 2003, 68: 9371.
[117] Weng, J. Y.; Wang, C. M.; Li, H. R.; Wang, Y. [J].Green Chem. 2006, 8:96.
[118] A. Davoodnia, M. Bakavoli, R. Moloudi, M. Khashi, N. Tavakoli-Hoseini [J]. Chinese Chemical Letters 2010, 21: 1.
[119] Abdol R. Hajipour, Yosof Ghayeb, Nafisehsadat Sheikhan, Arnold E. Ruoho. [J].Tetrahedron Letters 2009, 50 5649.
[120] Elise-Marie Dukuzeyezu Herve′Lefebvre, Martine Tessier, Alain Fradet. [J]. Polymer 2010, 51 1218.
[121] Rogers, R. D.; Seddon, K. R. [J].Science 2003, 302: 792
[122] BASF-BASIL process, 2007; http://www2.basf.de/en/intermed/nbd/products/ ionic_liquids
[1] Cole A.C., Jensen J.L., Ntai I, etal. [J].J. Am .Chem. Soc., 2002, 124: 5962.
[2]张所波,丁孟贤,高连勋. [J].有机化学,2002,22(3):159.
[3] Hua-Ping Zhu, Fan Yang. [J]. Green Chemistry, 2003, 5: 38>
[4] Brunelle,D.J.;scotia,N.Y. US Pat, 5229482 (1993)
[5] Brunelle D.J.;scotia,N.Y.US Pat.5229482 (1993).
[6] Huang J.; Jiang T.; Gao H.; Han B.; Liu Z.; Wu W.; Chang Y.; Zhao G., [J].Angew. Chem. Int. Ed, 2004, 43: 1397.
[7] Brunelle D. J.; scotia N. Y., US Pat, 5082968 (1992).
[8] Barton D. H.; Elliott J. D.; Géro S. D. [J]. J. Chem. Soc. Perkin. Trans. I 1982, 2085
[9] Isobe T.; Fukuda K.; Ishikawa T. [J].Tetrahedron: Asymmetry, 1998, 9: 1729
[10] Isobe T.; Fukuda K.; Ishikawa T., [J].J. Org. Chem. 2000, 65: 7770.
[11] Schlama T.; Gouverneur V.; Valleix A.; Greiner A.; Toupet L.; Mioskowlki C.; [J].J. Org. Chem. 1997, 62: 4200.
[12] Hua-Ping Zhu, Fan Yang, Jie Tang Ming-Yuan He [J]. Green Chemistry, 2003, 5: 38.
[13] A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J.Weaver, D.C. Forbes, J.H. Davis Jr. [J]. J. Am. Chem. Soc. 2002, 124: 5962.
[1] Ritter, J. J.; Minieri, P. P. [J]. J. Am. Chem. Soc. 1948, 70: 4045.
[2] Benson, F. R; Ritter, J. J. [J]. J. Am. Chem. Soc. 1949, 71: 4128.
[3] Reddy, K. L. [J]. Tetrahedron Lett. 2003, 44: 1453.
[4] Olah, G. A.; Yamato, T.; Iyer, P. S.; etal. [J]. Mater. Chem. Phys. 1987, 17:21.
[5] Polshettiwar, V.; Varma, R. S. [J]. Tetrahedron Lett. 2008, 49: 2661.
[6] Martinez, A. G.; Alvarez, R. M.; Vilar, E. T.; etal. [J]. Tetrahedron Lett. 1989, 30: 581.
[7] Firouzabadi, H.; Sardarian, A. R.; Badparva, H. [J]. Synthetic Commun. 1994, 601.
[8] Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. [J]. J . Org . Chem. 1995, 60: 2670.
[9] Mukhopadhyay, M.; Iqbal, J. [J].J .Org .Chem.1997, 62: 1843.
[10] Sharghi, H.; Niknam, K. [J]. Iran J. Chem. Chem. Eng. 1999, 18: 36.
[11] Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. [J].Tetrahedron .2000, 56:3077.
[12] Chen, X.; Okuhara, T. [J]. J. Catal. 2002, 207: 194.
[13] Salehi, P.; Motlagh, A. P. [J]. Synthetic. Commun. 2000, 671.
[14] Lakourag, M. M.; Movassagh, B.; Fasihi, [J]. Synthetic. Commun. 2000, 821.
[15] Okuhara, T.; Chen, X.; Matsuda, H. [J]. Appl. Catal. A: Gen. 2000, 200: 109.
[16] Callens, E.; Burton, A. J.; Barrett, A. G. M. [J]. Tetrahedron Lett. 2006, 47: 8699.
[17] Tamaddon, F.; Khoobi, M.; Keshavarz, E. [J]. Tetrahedron Lett. 2007, 48: 3643.
[18] Firouzabadi, H.; Iranpoor, N.; Khoshnood, A. [J]. Catal.Commun. 2008, 9: 529.
[19] Yadav, J. S.; Reddy, B. V. S.; Pandurangam, T.; etal. [J]. Catal.Commun. 2008, 9: 1297.
[20] Bruno Anxionnat, [J]. [J]. Tetrahedron Letters, 2009, 02: 1
[21] Clément Cazorla, Estelle Métay, Bruno Andrioletti, Marc Lemaire. [J].Tetrahedron Letters 2009, 50: 6855.
[22] (a) Maillard, M. C.; Hom, R. K.; Benson, T. E.; Moon, J. B.; Mamo, S.; Bienkowski, M.; Tomasselli, A. G.; Woods, D. D.; Prince, D. B.; Paddock, D. J.; Emmons, T. L.;Tucker, J. A.; Dappen, M. S.; Brogley, L.; Thorsett, E. D.; Jewett, N.; Sinha, S.;John, V. [J].J. Med. Chem. 2007, 50: 776. (b) Liao, Y. F.; Wang, B.-J.; Hsu, W. M.; Lee,H.; Liao, C. Y.; Wu, S. Y.; Cheng, H. T.; Hu, M. K. Mol. [J]. Pharmacol. 2007, 71: 588.(c) Bakshi, P.; Wolfe, M. S. [J].J. Med. Chem. 2004, 47:6485.
[23] (a) Beaulieu, P. L.; Wernic, D.; Abraham, A.; Anderson, P. C.; Bogri, T.; Bousquet,Y.; Croteau, G.; Guse, I.; Lamarre, D.; Liard, F.; Paris, W.; Thibeault, D. [J]. J. Med.Chem. 1997, 40: 2164. (b) Kempf, D. J.; Codavoci, L.; Wang, X. C.; Kohlbrenner,W. E.; Wideburg, N. E.; Saldivar, A.; Vasavanonda, S.; Marsh, K. C.; Bryant, P.;Sham, H. L.; Green, B. E.; Betebenner, D. A.; Erickson, J.; Norbeck, D. W. [J]. J. Med.Chem. 1993, 36: 320.(c) Medou, M.; Priem, G.; Rocheblave, L.; Pepe, G.; Meyer,M.; Chermann, J. C.; Kraus, J. L. Eur. [J]. J. Med. Chem. 1999, 34: 625.
[24] (a) Lee, C. E.; Kick, E. K.; Ellman, J. A. [J].J. Am. Chem. Soc. 1998, 120: 9735; (b) Kick,E. K.; Roe, D. C.; Geoffrey Skillman, A.; Liu, G.; Ewing, T. J. A.; Sun, Y.; Kuntz, I. D.;Ellman, [J]. J. A. Chem. Biol. 1997, 4: 297.
[25] Haque, T. S.; Geoffrey Skillman, A.; Lee, C. E.; Habashita, H.; Gluzman, I. Y.;Ewing, T. J. A.; Goldberg, D. E.; Kuntz, I. D.; Ellman. [J].J. A. J. Med. Chem. 1999, 42: 1428.
[26] Concellón, J. M.; Suárez, J. R.; Del Solar, V. [J]. J. Org. Chem. 2005, 70: 7447.
[27] Mickael Dos Santos, Benoit Crousse , Danièle Bonnet-Delpon [J].Tetrahedron Letters 2009, 50: 857.
[28] Kristof Van Emelen,? Tom De Wit, Georges J. Hoornaert, and Frans Compernolle [J]. Org. Lett., 2000, 2: 3083.
[29] Kristof Van Emelen, Tom De Wit, Georges J. Hoornaert, Frans Compernolle , [J]. Tetrahedron 2002, 58: 4225.
[30] Jose′M. Concello′N, Estela Riego, Jose′Ramo′n Sua′rez, Santiago Garc ?′a -Granda, M. Rosario D?′az [J]. Org. Lett., , 2004 , 6: 4499.
[31] J.S. Yadav , [J]. Tetrahedron 2008, 64: 3025.
[32] J. S. Yadav, [J].Tetrahedron Letters 2007, 48: 4903.
[33] Vijay Nair, Roshini Rajan, Nigam P. Rath. [J]. Org. Lett. 2002, 4: 1575.
[34] Oleg L. Epstein , Tomislav Rovis. [J]. J. Am. Chem. soc. 2006,128: 16480.
[35] Gowravaram Sabitha , M. Bhikshapathi , Sambit Nayak , J. S. Yadav , R. Ravi , A. C. Kunwar [J]. Tetrahedron Letters 2008, 49: 5727.
[36] Cole, A. C.; Jensen, J. L.; Ntai, L.; etal. [J].J. Am. Chem. Soc. 2002, 124: 5962.
[37] Zhu, H. P.; Yang, F.; Tang, J.; He, M.Y. [J]. Green.Chem. 2003, 5: 38.
[38] Xing, H.; Wang, T.; Zhou, Z.; etal. [J]. Ind. Eng. Chem. Res. 2005, 44: 4147.
[39] Fang, D.; Zhou, X.; Ye, Z.; Liu, Z. L. [J]. Ind. Eng. Chem. Res. 2006, 45: 7982.
[40] Du, D.; Ji, S.; Jang, Z. [J]. Synlett. 2005, 959.
[41] Callens, E.; Burton, A. J.; Barrett, A. G. M. [J].Tetrahedron Lett. 2006, 47: 8699.
[42] Firouzabadi, H.; Iranpoor, N.; Khoshnood, A.Catal.Commun. 2008, 9, 529.
[1] J. Pinnow and G. Pistor, Ber. Deut. Chem. Ges., 1894, 27: 602.
[2] J. Pinnow, Ber. Deut. Chem. Ges. 1895, 28: 3039
[3] J. Pinnow, Ber. Deut. Chem. Ges. 1897, 30: 3119.
[4] J. Pinnow, Ber. Deut. Chem. Ges. 1898, 31: 2982.
[5] J. Pinnow, Ber. Deut. Chem. Ges. 1899, 32: 1666.
[6] A. Schuster and J. Pinnow, Ber. Deut. Chem. Ges. 1896, 29: 1053.
[7] METH-COHN 0, [J].Advances in Heterocyclic Chemistry, 1972,14:211.
[8] V, PE工NADOR C, [J].Synthesis, 1993, 152.
[9] OJEA V, [J].Synlett, 1995, 622.
[10] OJEA V, [J].Tetrahedron, 1998, 54: 927.
[11] CHANTEGREL B, DESHAYES C, [J].Tetrahedron Letters, 1995, 36:7859.
[12] TVERDOKHLEBOV A V, GORLLYA A P etal. [J].Tetrahedron, 2006, 62: 9146.
[13] KAVA N, HALASZ-DAJKA B,VO-THANH G,etal. [J].Tetrahedron,2005 61: 9052.
[14] SCHWART A, BEKE G, KOVARI Z, etal. [J]. Journal of Molecular Structure: 2000, 528: 49.
[15] Petra Dunkel , Gyorgy Turos, Attila Benyei, Krisztina Ludanyi, Peter Matyus. [J]. Tetrahedron 2010, 66: 2331.
[16] O. V. Ryabtsova, A. F. Pozharskii, A. V. Degtyarev and V. A. Ozeryanskii, Mendeleev Commun., 2006, 313.
[17] (a) Meth-Cohn, O.; Naqui, M. A. [J]. Chem. Commun. 1967, 1157..(b) Grantham, R. K.; Meth-Cohn, O. [J]. Chem. Commun. 1968, 500. (c) Grantham, R. K.; Meth-Cohn, O.; Naqui, M. A. [J]. J. Chem. Soc., C 1969, 1438. (d) Grantham, R. K.; Meth-Cohn, O. [J]. J. Chem. Soc., C 1969, 1444.
[18] Zhang, C.; De, C. K.; Mal, R.; Seidel, D. [J]. J. Am. Chem. Soc. 2008, 130: 416.
[19] Verboom, W.; Hamzink, M. R. J.; Reinhoudt, D. N.; Visser, R. [J]. Tetrahedron Lett. 1984, 25: 4309.
[20] Chen Zhang; Sandip Murarka; Daniel Seidel. [J]. J. Org. Chem. 2009, 74: 419.