吡咯-2-甲醛化合物的缩醛交换反应和醚化反应研究
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摘要
由于吡咯类杂环化合物在有机化学和药物化学领域的重要地位以及吡咯类化合物反应性质的复杂性,为有机化学理论创新和药物合成既带来了机遇,同时也带来了挑战。我们在合成吡咯类潜在药物分子过程中发现的缩醛交换反应及醚化反应是两个新型的有机反应,而且转化产率高,反应条件温和,操作简单易行,具有广泛的适用性,因此必将丰富和拓展有机化学尤其是吡咯化学的知识领域,而且在有机合成化学当中也将发挥一定的作用。本论文系统研究了吡咯-2-甲醛化合物的缩醛交换反应及醚化反应的反应条件、适用范围及反应机理,共包括以下三章：
第1章,综述了缩醛(酮)的制备以及在有机合成中的应用。
第2章,系统研究了吡咯-2-甲醛缩醛化合物在醇钠的醇溶液中的缩醛交换反应。首先考察了吡咯-2-甲醛缩醛化合物在碱性条件下的缩醛交换反应的反应条件及适用范围,发现吡咯-2-甲醛缩醛化合物的缩醛交换反应与吡咯环上的H紧密相关；其次根据实验结果提出了可能的反应机理。
第3章,系统研究了吡咯-2-甲醛化合物在醇溶液中还原成醚的反应。首先探索了不同的吡咯-2-甲醛化合物在对甲苯磺酸催化剂存在下在醇溶液中的反应情况,发现吡咯-2-甲醛化合物在醇溶液中的还原成醚反应可能跟醛与醇反应生成缩醛的反应是一对竞争反应,而竞争的结果依赖于吡咯环上的电子云密度；其次根据实验现象和实验结果提出了可能的反应机理。
Pyrrole compound is very important in organic synthesis and medicinal chemistry. Some reactivity of pyrrolic compounds are still unknown to organic chemists, so the investigaion on pyrrole compounds will bring them opportunities to make some achievements in the aspects of theory innovation and drug synthesis. In the course of study on the synthesis of pyrrole compounds with potential bioactivity, we found a new type of transacetalization of pyrrole-2-carbaldehyde with sodium alkoxides and a new type of etherification of pyrrole-2-carbaldehyde with alcohols, which have the advantages of high yield, mild reaction condition, labile work-up, and broad application scope. Therefore, our results will contribute to broadening the knowledge of pyrrole chemistry and also will find some applications in organic synthesis. In this thesis, the optimization of reaction conditions, application scope and mechanism of transacetalization of pyrrole-2-carbaldehyde with sodium alkoxides and etherification of pyrrole-2-carbaldehyde with alcohols will be described. It contains three chapters as below:
Chapter 1, the preparation of acetals and their application in organic synthesis were reviewed.
Chapter 2, the transacetalization of pyrrole-2-carbaldehyde in alkaline media was described in detail. We firstly optimized the reaction conditions of transacetalization of pyrrole-2-carbaldehyde with sodium alkoxide. Then, we studied its application scope. Finally, we proposed a possible mechanism to interpret the transacetalization. Our results showed that existance of the free hydrogen at nitrogen atom of pyrrole ring was the most important, and a mechanism in relation to azafulvene was proved by our experiments.
Chapter 3, a new type of etherification through the reduction of pyrrole-2-carbaldehyde with alcohol was described. We explored the reduction of a few of pyrrole-2-carbaldehyde substrates with alcohol in the presence of para- toluenesulphonic acid as catalyst. Experimental results showed that etherification of pyrrole-2-carbaldehyde with alcohol may compete with acetalization of pyrrole-2-carbaldehyde with alcohol, and the electron density on pyrrole ring will control what product will be finally formed. A possible mechanism was also proposed.
第1章,综述了缩醛(酮)的制备以及在有机合成中的应用。
第2章,系统研究了吡咯-2-甲醛缩醛化合物在醇钠的醇溶液中的缩醛交换反应。首先考察了吡咯-2-甲醛缩醛化合物在碱性条件下的缩醛交换反应的反应条件及适用范围,发现吡咯-2-甲醛缩醛化合物的缩醛交换反应与吡咯环上的H紧密相关；其次根据实验结果提出了可能的反应机理。
第3章,系统研究了吡咯-2-甲醛化合物在醇溶液中还原成醚的反应。首先探索了不同的吡咯-2-甲醛化合物在对甲苯磺酸催化剂存在下在醇溶液中的反应情况,发现吡咯-2-甲醛化合物在醇溶液中的还原成醚反应可能跟醛与醇反应生成缩醛的反应是一对竞争反应,而竞争的结果依赖于吡咯环上的电子云密度；其次根据实验现象和实验结果提出了可能的反应机理。
Pyrrole compound is very important in organic synthesis and medicinal chemistry. Some reactivity of pyrrolic compounds are still unknown to organic chemists, so the investigaion on pyrrole compounds will bring them opportunities to make some achievements in the aspects of theory innovation and drug synthesis. In the course of study on the synthesis of pyrrole compounds with potential bioactivity, we found a new type of transacetalization of pyrrole-2-carbaldehyde with sodium alkoxides and a new type of etherification of pyrrole-2-carbaldehyde with alcohols, which have the advantages of high yield, mild reaction condition, labile work-up, and broad application scope. Therefore, our results will contribute to broadening the knowledge of pyrrole chemistry and also will find some applications in organic synthesis. In this thesis, the optimization of reaction conditions, application scope and mechanism of transacetalization of pyrrole-2-carbaldehyde with sodium alkoxides and etherification of pyrrole-2-carbaldehyde with alcohols will be described. It contains three chapters as below:
Chapter 1, the preparation of acetals and their application in organic synthesis were reviewed.
Chapter 2, the transacetalization of pyrrole-2-carbaldehyde in alkaline media was described in detail. We firstly optimized the reaction conditions of transacetalization of pyrrole-2-carbaldehyde with sodium alkoxide. Then, we studied its application scope. Finally, we proposed a possible mechanism to interpret the transacetalization. Our results showed that existance of the free hydrogen at nitrogen atom of pyrrole ring was the most important, and a mechanism in relation to azafulvene was proved by our experiments.
Chapter 3, a new type of etherification through the reduction of pyrrole-2-carbaldehyde with alcohol was described. We explored the reduction of a few of pyrrole-2-carbaldehyde substrates with alcohol in the presence of para- toluenesulphonic acid as catalyst. Experimental results showed that etherification of pyrrole-2-carbaldehyde with alcohol may compete with acetalization of pyrrole-2-carbaldehyde with alcohol, and the electron density on pyrrole ring will control what product will be finally formed. A possible mechanism was also proposed.
引文
[1]C. E. Loader, H. J. Anderson, Synthesis 1978,295～297
[2]王倩,王芹珠,方方,等.精细化工1994,11(4)1415
[3]Melvin S. Newman and Robert J. Harper, J. Am. Chem. Soc.1958,80,6350-6355
[4]W. Reusch et al., J. Org. Chem.1979,44,3666
[5]P. S. Clezy, C. J. R. Fookes et al, Aust. J. Chem.1974,27,357-369
[6]Habib Firouzabadi, Nasser Iranpoor, Babak Karimi, synlett.1999,3,321-323
[7]James D. White, F. W. J. Demnitz, Hirohisa Oda, et al., Org. Lett.2000,2(21)3313-3316
[8]Lee S. H., Lee J. H., Yoon C. M., Tetrahedron Lett.2002,43,2699
[9]K. Moedritzer, J. R. Van Wazer, J. Org. Chem.1965,30,3925
[10]C. Piantadosi et al., J. Am. Chem. Soc.1958,80,6613
[11]W. L. Howard, N. B. Lorette, J. Org. Chem.1960,25,525
[12]C. Piantadosi et al., J. Pharm. Sci.1964,53,1024
[13]G. L. Larson, A. Hernandez, J. Org. Chem.1973,38,3935
[14]N. Blackett et al., Tetrahedron 1970,26,1311
[15]R. P. Hanzlik, M. Leinwetter, J. Org. Chem.1978,43,438
[16]F. Nerdel et al., Justus Liebigs Ann. Chem.1967,85,710
[17]Jean-Laurent Paparin, Eur. J. Org. Chem.2000,3909-3918
[18]S. K. De, R. A. Gibbs, Tetrahedron Letters 2004,45,8141-8144
[19]Leonard N. M., Oswald M. C., Freiberg D. A. et al., J. Org. Chem.2002,67,5202
[20]R.Kumar, A. K.Chakraborti, Tetrahedron Letters 2005,46,8319-8323
[21]Nao Hamada, Kiyoshi Kazahaya, Hisashi Shimizu, et al., Synlett.2004,6,1074-1076
[22]S. Velusamy, T. Punniyamurthy, Tetrahedron Letters 2004,45,4917-4920
[23]Ranu B. C., Jana R., Samanta S., Adv. Synth. Catal. 2004,346-446
[24]Brian T. Gregg, Kathryn C. Golden, John F. Quinn, Tetrahedron 2008,64,3287-3295
[25]Amos B. Smith, Ⅲ, Mineo Fukui, Henry A. Vaccaro, et al., J. Am. Chem. Soc.1991,113(6), 2071-2092
[26]D. Scott Coffey, Andrew I. McDonald, et al., J. Am. Chem. Soc.1999,121,6944-6945
[27]王存德,杨新华,钱文元,精细化工 1992,9(1),426
[28]Ken-ichi Shimizu, Eidai Hayashi, et al., Tetrahedron Letters 2004,45,5135-5138
[29]吕月仙.郑州轻工学院学报1999,14(1),60-63
[30]Tomonori Kawabata, Tomoo Mizugaki, Kohki Ebitani et al., Tetrahedron Letters 2001,42, 8329-8332
[31]Ji, S.-J., Wu, L. J., Mol. Catal. A:Chem.2003,202,41
[32]Hai-Hong Wu, Fan Yang, Peng Cui, Jie Tang et al., Tetrahedron Letters 2004,45, 4963-4965
[33]Nabajyoti Deka, Dipok J. Kalita, Ruli Borah, et al., J. Org. Chem.1997,62(5),1563-1564
[34]文瑞明,游沛清,罗新湘,俞善信.石油化工2002,31(5),373-375
[35]Gopinath, R., Haque, S. J., Patel, B. K., J. Org. Chem.2002,67,5842-5845
[36]Rangam Gopinath, SK.Jiaul Haque, and Bhisma K. Patel, J. Org. Chem.2002,67(16), 5842-5845
[37]赵立芳,王宏社,苗建英,有机化学2008,28(10),1792-1796
[38]Babak Karimi, Hassan Seradj and Jafar Maleki, Tetrahedron 2002,58,4513-4516
[39]Karimi, B., Ebrahimian, G. R., Seradj, H., Org. Lett.1999,1,1737-1739
[40]Karimi, B., Hazarkhani, H., Maleki, J., Synthesis 2005,279-285
[41]J. G. Aston and R. B. Greenburg, J. Am. Chem. Soc.1940,62,2590-2595
[42]Michal Barbasiewicz and Mieczyslaw Maukosza, Org. Lett.2006,8(17),3745-3748
[43]H. E. Simmons, D. W. Wiley, J. Am. Chem. Soc.1960,82,2288
[44]H. Bredereck, F. Effenberger, G. Simchen, Angew. Chem.1961,73,493
[45]H. Bredereck, F. Effenberger, G. Simchen, Chem. Ber.1963,96,1350
[46]H. Bredereck et al., Chem. Ber.1968,101,41
[47]E. J. Corey, T. Hase, Tetrahedron Lett.1975,3267
[48]R. M. Munavu, H. H. Szmant, Tetrahedron Lett.1975,4543
[49]Williams E. R., Jass P.A., Allan Tse T. L., Gaston R. D., J. Am. Chem. Soc.1990,112,4552
[50]Babak Karimi, G. Reza Ebrahimian, Hassan Seradj, Organic Letters 1999,1(11),1737-1739
[51]G. V. M. Sharma, K. Laxma Reddy, P. Sree Lakshmi et al., Tetrahedron Letters 2004,45, 9229-9232
[52]T. Benneche, Synthesis 1995,1
[53]A. F. Kluge, K. G. Untch, and J. H. Fried, J. Am. Chem. Soc.1972,94,7827
[54]B. C. Ranu, A. Majee and A. R. Das, Synth. Commun.1995,25,363
[55]P. Kumar, S. V. N. Raju, R. S. Reddy, B. Pandey, Tetrahedron Lett.1994,35,1289
[56]E. J. Corey, J.-L. Gras, and P. Ulrich, Tetrahedron Lett.1976,17,809
[57]Edwin Vedejs, Jeremy D. Little, Lisa M. Seaney, J. Org. Chem.2004,69,1788-1793
[58]Greene TW, Wuts P GM., Protective Group s in Organic Synthesis John Wiley & Sons,New York,1999
[59]赵知中,周瑾,鲁桂琛,等有机化学中的保护基团 北京：科学出版社,1984
[60]D. M. Pore, U. V. Desai, R. B. Mane, and P. P. Wadgaonkar, Synth. Commun.2004,34, 2135
[61]T. Nishiguchi, S. Hayakawa, Y. Hirasaka, M. Saitoh, Tetrahedron Lett.2000,41,9843
[62]R. J. Petroski, Synth. Commun.2003,33,3251
[63]K. F. Bernady, M. B. Floyd, J. F. Poletto, M. J. Weiss, J. Org. Chem.1979,44,1438
[64]M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem.1977,42,3772
[65]A. Bongini, G.Cardillo, M.Orena, S.Sandri, Synthesis 1979,618
[66]R. D. Johnston, C. R. Marston, P. E. Krieger, G. L. Goe, Synthesis 1988,393
[67]S. Hoyer, P. Laszlo, M. Orlovic, E. Polla, Synthesis 1986,655
[68]T. Taniguchi, K. Kadota, A. S. Eiazab, K. Ogasawara, Synlett.1999,1247
[69]H. M. S. Kumar, B. V. S. Reddy, E. J. Reddy, J. S. Yadav, Chem. Lett.1999,28,857
[70]N. Deka and J. C. Sarma, J. Org. Chem.2001,66,1947
[71]Nabajyoti Deka and Jadab C. Sarma, J. Org. Chem.2001,66,1947-1948
[72]NaoiHoamada, Tsuneo Sato, Synlett.2004,10,1802-1804
[73]B. C. Ranu and M. Saha, J. Org. Chem.1994,59,8269
[74]Sarala Naik, Rangam Gopinath and Bhisma K. Patel, Tetrahedron Letters 2001,42, 7679-7681
[75]J. M. Campelo, A. Garcia, F. Lafont, D. Luna, and J. M. Marinas, Synth. Commun.1992,22, 2335
[76]B. P. Bandgar and S. P. Kasture, J. Chinese Chem. Soc. (Taipei, Taiwan) 2001,48,877
[77]M. M. Heravi, F. K. Behbahani, H. A. Oskooie, and R. H. Shoar, Tetrahedron Lett.2005,46, 2543
[78]Bhalerao U T, Davis K J, Rao B V., Synth. Commun.1996,26(16),3081
[79]Abu T. Khan, Lokman H. Choudhury and Subrata Ghosh, Tetrahedron Letters 2004,45, 7891-7894
[80]Bahman Tamami and Kaveh Parvanak Borujeny, Tetrahedron Letters 2004,45,715-718
[81]Vasudevan V. Namboodiri and Rajender S. Varma, Tetrahedron Letters 2002,43, 1143-1146
[82]Ma S, V enanzi L. M., Tetrahedron Lett.1993,34(33),5269
[83]Tomoko Mineno, Tetrahedron Letters 2002,43,7975-7978
[84]G. Maity and S. C. Roy, Synth. Commun.1993,23,1667
[85]K. Tanemura, T. Horaguchi, and T. Suzuki, Bull. Chem. Soc. Jpn.1992,65,304
[86]J. D. Prugh and W. C. McCarth, Tetrahedron Lett.1966,1351
[87]T. L. Huller and S. B. Siskin, J. Org. Chem.1970,35,225
[88]D. A. Seeley and J. McElwee, J. Org. Chem.1973,38.1691
[89]T. L. Hullar and S. B. Siskin, The Journal of Organic Chemistry 1970,36(1),225-228
[90]James W. Wilt, Mehboob Peeran, J. Org. Chem.1986,51(13),2618-2619
[91]Peter M. Collins, Ajay Manro, Ethel C. Opara-Mottah, et al., J. Chem. Soc., Chem. Commun. 1988,272-274
[92]Sidhaghatta D. Venkataramu, James H. Cleveland, et al., J. Org. Chem.1979,44(17), 3082-3084
[93]Lin Hai-xia, Xu Liang-heng, Huang Nai-ju, Synthetic communications 1997,27(2),303-306
[94]Tadashi Aoyama, Toshio Takido and Mitsuo Kodomari, Tetrahedron letters 2005,46, 1989-1992
[95]Shinsei Sayama, Tetsuo Onami, Synlett.2004,15,2739-2745
[96]Lawrence C.Anderson, Harold W. Pinnick, J. Org. Chem.1978,43(17),3417-3418
[97]Saburo Sugai, Takashi Kodama, Sanya Akaboshi, and Shiro Ikegami, Chem. Pharm. Bull. 1984,32(1),99-105
[98]Hakjune Rhee and Jin Yeon Kim, Bull. Korean Chem. Soc.2000,21(3),355-357
[99]B. Karimi, J. Rajabi, Journal of Molecular Catalysis A:Chemical 2005,226,165-169
[100]par Francis Barbot et Philippe Miginiac, Helvetica Chimica Acta 1979,62(5),1451-1457
[101]Christian Reichardt, Abdel-Rahman Ferwanah, et al., Liebigs Ann. Chem.1984,649-679
[102]Manish Dixit, Brajendra K. Tripathi, Akhilesh K. Tamrakar et al., Bioorganic & Medicinal Chemistry 2007,15,727-734
[103]V. G. Saraswathy and S. Sankararaman, J. Org. Chem.1994,59,4665
[104]H.Firouzabadi,N.Iranpoor and B. Karimi, Synlett.1998,739
[105]S. Samajdar, M. K. Basu, F. F. Backer and B. K. Banik, Tetrahedron Lett.2001,42,4425
[106]Sarala Naik, Rangam Gopinath, Mousumi Goswami et al., Org. Biomol. Chem.2004,2, 1670-1677
[107]Das B., Ramu R., Reddy M. R., Mahender G., Synthesis 2005,250
[108]Firouzabadi H., Iranpoor N., Amani K., Synthesis 2002,59
[1]The pophyrin Handbook Vol.1-10, Academic Press, New York,2000; The pophyrin Handbook Vol.11-20, Academic Press, New York,2004
[2]Sessler J. L., Anzenbacher P. Jr., Jursikova K., et al., Pure Appl. Chem.1998,70,2401
[3]Turner B., Shterenberg A., Kapon M., et al., Chem. Commun.2001,13
[4]Harriman A., Mehrabi M., Maiya B. G., Photochem. Photobiol. Sci.2005,4,47
[5]Namor A. F. D., Abbas I., Hammud H. H., J. Phys. Chem. B 2007,111,3098
[6]Scott T. Handy, Yanan Zhang, and Howard Bregman, J. Org. Chem.2004,69 (7), 2362-2366
[7]Haruhisa Kikuchi, Mizuki Sekiya, Yasuhiro Katou, Org. Lett.2009,11(8),1693-1695
[8]Kenza Dairi, Yuxing Yao, Michael Faley, Org. Process Res. Dev.2007,11(6),1051-1054
[9]Tsutomu Fukuda, Ei-ichi Sudo, Kozue Shimokawa, et al., Tetrahedron 2008,64,328-338
[10]Charles E. Loader, Graham H. Barnett, and Hugh J. Anderson, Can. J. Chem.1982,60, 383-389
[11]M. F. Hudson, K. M. Smith, Synthesis 1976,464-467
[12]Charles E. Loader, Hugh J. Anderson, Synthesis 1978,295-297
[13]陈金泰,陈耀焕,盛怀禹.有机化学1988,8,164-166
[14]Hermann K. Hombrecher, Gaby Horter, Synthesis 1990,389-391
[15]Franz-Peter Montforts, Ulrich M. Schwartz, Liebigs Ann. Chem.1985,2301-2303
[16]Robert M. Silverstein, Edward E. Ryskiewicz, et al., J. Org. Chem.1955,20(5),668-672
[17]Hugh J. Anderson, Can. J. Chem.1957,35,21-27
[18]Philip E. Sonnet, J. Org. Chem.1971,36(7),1005-1007
[19]Jutz C., Kirchlechner R., Siedel H. J., Chem. Ber.1969,102,2301
[20]John T. Gupton, Dale A. Krolikowski, Richard H. Yu, J. Org. Chem.1990,55(15), 4735-4740
[21]Kevin M. Smith, Michiko Miura, and Hani D. Tabba, J. Org. Chem.1983,48(24), 4779-4781
[1]J. Seyden-Penne, Reductions by the Alumino- and Borohydrides in Organic Synthesis VCH Publishers, New York,1991.
[2]H. C. Brown and R. F. McFarlin, J. Am. Chem. Soc.1956,78,752
[3]H. C. Brown and B. C. SubbaRao, J. Am. Chem. Soc.1958,80,5377
[4]H. C. Brown and A. Tsukamoto, J. Am. Chem. Soc.1964,86,1089
[5]M. Freifelder, Catalytic Hydrogenation in Organic Synthesis:Procedures and Commentary John Wiley & Sons, New York,1978
[6]Clemmensen E. Ber., Dtsch. Chem. Ges 1913,46,1837
[7]Kadam A. J., Baraskar U. K., Mane R. B., Indian J. Chem. Sect. B 2000,39B,822
[8]Kohara T., Tanaka H., Kimura K., Synthesis 2002,355
[9]Wolff L., Justus Liebigs Ann. Chem.1912,394,86
[10]Huang-Minlong, J. Am. Chem. Soc.1946,68,2487
[11]Bashore C. G.., Samardjiev I. J., J. Am. Chem. Soc.2003,125,3268
[12]Michael P. Doyle, Donald J. DeBruyn, Dale A. Kooistra, J. Am. Chem. Soc.1972,94, 3659-3661
[13]Olah G. A., Narang S. C., Meidar D., Salem G., Synthesis 1981,282
[14]George A. Olah, Takehiko Yamato, Pradeep S. Iyer, et al., J. Org. Chem.1986,51, 2826-2828
[15]Ernest L. Eliel, Mark Rerick, J. Org. Chem.1958,23,1088
[16]Abdun-Nur, A. R., Issidorides C.H., J. Org. Chem.1962,27,67-70
[17]Fleming B., Bolker H. I., Can. J. Chem.1974,52,888-893
[18]Tsunoda T., Suzuki M., Noyori R., Tetrahedron Lett.1979,48,4679-4680
[19]Home D.A., Jordan A., Tetrahedron Lett.1978,16,1357-1358
[20]N. Xavier and S. J. Arulraj, Tetrahedron 1985,41(14),2875-2878
[21]Munetaka Kunishima, Daisuke Nakata, Chem.Pharm.Bull. 2001,49(1),97-100
[2]王倩,王芹珠,方方,等.精细化工1994,11(4)1415
[3]Melvin S. Newman and Robert J. Harper, J. Am. Chem. Soc.1958,80,6350-6355
[4]W. Reusch et al., J. Org. Chem.1979,44,3666
[5]P. S. Clezy, C. J. R. Fookes et al, Aust. J. Chem.1974,27,357-369
[6]Habib Firouzabadi, Nasser Iranpoor, Babak Karimi, synlett.1999,3,321-323
[7]James D. White, F. W. J. Demnitz, Hirohisa Oda, et al., Org. Lett.2000,2(21)3313-3316
[8]Lee S. H., Lee J. H., Yoon C. M., Tetrahedron Lett.2002,43,2699
[9]K. Moedritzer, J. R. Van Wazer, J. Org. Chem.1965,30,3925
[10]C. Piantadosi et al., J. Am. Chem. Soc.1958,80,6613
[11]W. L. Howard, N. B. Lorette, J. Org. Chem.1960,25,525
[12]C. Piantadosi et al., J. Pharm. Sci.1964,53,1024
[13]G. L. Larson, A. Hernandez, J. Org. Chem.1973,38,3935
[14]N. Blackett et al., Tetrahedron 1970,26,1311
[15]R. P. Hanzlik, M. Leinwetter, J. Org. Chem.1978,43,438
[16]F. Nerdel et al., Justus Liebigs Ann. Chem.1967,85,710
[17]Jean-Laurent Paparin, Eur. J. Org. Chem.2000,3909-3918
[18]S. K. De, R. A. Gibbs, Tetrahedron Letters 2004,45,8141-8144
[19]Leonard N. M., Oswald M. C., Freiberg D. A. et al., J. Org. Chem.2002,67,5202
[20]R.Kumar, A. K.Chakraborti, Tetrahedron Letters 2005,46,8319-8323
[21]Nao Hamada, Kiyoshi Kazahaya, Hisashi Shimizu, et al., Synlett.2004,6,1074-1076
[22]S. Velusamy, T. Punniyamurthy, Tetrahedron Letters 2004,45,4917-4920
[23]Ranu B. C., Jana R., Samanta S., Adv. Synth. Catal. 2004,346-446
[24]Brian T. Gregg, Kathryn C. Golden, John F. Quinn, Tetrahedron 2008,64,3287-3295
[25]Amos B. Smith, Ⅲ, Mineo Fukui, Henry A. Vaccaro, et al., J. Am. Chem. Soc.1991,113(6), 2071-2092
[26]D. Scott Coffey, Andrew I. McDonald, et al., J. Am. Chem. Soc.1999,121,6944-6945
[27]王存德,杨新华,钱文元,精细化工 1992,9(1),426
[28]Ken-ichi Shimizu, Eidai Hayashi, et al., Tetrahedron Letters 2004,45,5135-5138
[29]吕月仙.郑州轻工学院学报1999,14(1),60-63
[30]Tomonori Kawabata, Tomoo Mizugaki, Kohki Ebitani et al., Tetrahedron Letters 2001,42, 8329-8332
[31]Ji, S.-J., Wu, L. J., Mol. Catal. A:Chem.2003,202,41
[32]Hai-Hong Wu, Fan Yang, Peng Cui, Jie Tang et al., Tetrahedron Letters 2004,45, 4963-4965
[33]Nabajyoti Deka, Dipok J. Kalita, Ruli Borah, et al., J. Org. Chem.1997,62(5),1563-1564
[34]文瑞明,游沛清,罗新湘,俞善信.石油化工2002,31(5),373-375
[35]Gopinath, R., Haque, S. J., Patel, B. K., J. Org. Chem.2002,67,5842-5845
[36]Rangam Gopinath, SK.Jiaul Haque, and Bhisma K. Patel, J. Org. Chem.2002,67(16), 5842-5845
[37]赵立芳,王宏社,苗建英,有机化学2008,28(10),1792-1796
[38]Babak Karimi, Hassan Seradj and Jafar Maleki, Tetrahedron 2002,58,4513-4516
[39]Karimi, B., Ebrahimian, G. R., Seradj, H., Org. Lett.1999,1,1737-1739
[40]Karimi, B., Hazarkhani, H., Maleki, J., Synthesis 2005,279-285
[41]J. G. Aston and R. B. Greenburg, J. Am. Chem. Soc.1940,62,2590-2595
[42]Michal Barbasiewicz and Mieczyslaw Maukosza, Org. Lett.2006,8(17),3745-3748
[43]H. E. Simmons, D. W. Wiley, J. Am. Chem. Soc.1960,82,2288
[44]H. Bredereck, F. Effenberger, G. Simchen, Angew. Chem.1961,73,493
[45]H. Bredereck, F. Effenberger, G. Simchen, Chem. Ber.1963,96,1350
[46]H. Bredereck et al., Chem. Ber.1968,101,41
[47]E. J. Corey, T. Hase, Tetrahedron Lett.1975,3267
[48]R. M. Munavu, H. H. Szmant, Tetrahedron Lett.1975,4543
[49]Williams E. R., Jass P.A., Allan Tse T. L., Gaston R. D., J. Am. Chem. Soc.1990,112,4552
[50]Babak Karimi, G. Reza Ebrahimian, Hassan Seradj, Organic Letters 1999,1(11),1737-1739
[51]G. V. M. Sharma, K. Laxma Reddy, P. Sree Lakshmi et al., Tetrahedron Letters 2004,45, 9229-9232
[52]T. Benneche, Synthesis 1995,1
[53]A. F. Kluge, K. G. Untch, and J. H. Fried, J. Am. Chem. Soc.1972,94,7827
[54]B. C. Ranu, A. Majee and A. R. Das, Synth. Commun.1995,25,363
[55]P. Kumar, S. V. N. Raju, R. S. Reddy, B. Pandey, Tetrahedron Lett.1994,35,1289
[56]E. J. Corey, J.-L. Gras, and P. Ulrich, Tetrahedron Lett.1976,17,809
[57]Edwin Vedejs, Jeremy D. Little, Lisa M. Seaney, J. Org. Chem.2004,69,1788-1793
[58]Greene TW, Wuts P GM., Protective Group s in Organic Synthesis John Wiley & Sons,New York,1999
[59]赵知中,周瑾,鲁桂琛,等有机化学中的保护基团 北京：科学出版社,1984
[60]D. M. Pore, U. V. Desai, R. B. Mane, and P. P. Wadgaonkar, Synth. Commun.2004,34, 2135
[61]T. Nishiguchi, S. Hayakawa, Y. Hirasaka, M. Saitoh, Tetrahedron Lett.2000,41,9843
[62]R. J. Petroski, Synth. Commun.2003,33,3251
[63]K. F. Bernady, M. B. Floyd, J. F. Poletto, M. J. Weiss, J. Org. Chem.1979,44,1438
[64]M. Miyashita, A. Yoshikoshi, P. A. Grieco, J. Org. Chem.1977,42,3772
[65]A. Bongini, G.Cardillo, M.Orena, S.Sandri, Synthesis 1979,618
[66]R. D. Johnston, C. R. Marston, P. E. Krieger, G. L. Goe, Synthesis 1988,393
[67]S. Hoyer, P. Laszlo, M. Orlovic, E. Polla, Synthesis 1986,655
[68]T. Taniguchi, K. Kadota, A. S. Eiazab, K. Ogasawara, Synlett.1999,1247
[69]H. M. S. Kumar, B. V. S. Reddy, E. J. Reddy, J. S. Yadav, Chem. Lett.1999,28,857
[70]N. Deka and J. C. Sarma, J. Org. Chem.2001,66,1947
[71]Nabajyoti Deka and Jadab C. Sarma, J. Org. Chem.2001,66,1947-1948
[72]NaoiHoamada, Tsuneo Sato, Synlett.2004,10,1802-1804
[73]B. C. Ranu and M. Saha, J. Org. Chem.1994,59,8269
[74]Sarala Naik, Rangam Gopinath and Bhisma K. Patel, Tetrahedron Letters 2001,42, 7679-7681
[75]J. M. Campelo, A. Garcia, F. Lafont, D. Luna, and J. M. Marinas, Synth. Commun.1992,22, 2335
[76]B. P. Bandgar and S. P. Kasture, J. Chinese Chem. Soc. (Taipei, Taiwan) 2001,48,877
[77]M. M. Heravi, F. K. Behbahani, H. A. Oskooie, and R. H. Shoar, Tetrahedron Lett.2005,46, 2543
[78]Bhalerao U T, Davis K J, Rao B V., Synth. Commun.1996,26(16),3081
[79]Abu T. Khan, Lokman H. Choudhury and Subrata Ghosh, Tetrahedron Letters 2004,45, 7891-7894
[80]Bahman Tamami and Kaveh Parvanak Borujeny, Tetrahedron Letters 2004,45,715-718
[81]Vasudevan V. Namboodiri and Rajender S. Varma, Tetrahedron Letters 2002,43, 1143-1146
[82]Ma S, V enanzi L. M., Tetrahedron Lett.1993,34(33),5269
[83]Tomoko Mineno, Tetrahedron Letters 2002,43,7975-7978
[84]G. Maity and S. C. Roy, Synth. Commun.1993,23,1667
[85]K. Tanemura, T. Horaguchi, and T. Suzuki, Bull. Chem. Soc. Jpn.1992,65,304
[86]J. D. Prugh and W. C. McCarth, Tetrahedron Lett.1966,1351
[87]T. L. Huller and S. B. Siskin, J. Org. Chem.1970,35,225
[88]D. A. Seeley and J. McElwee, J. Org. Chem.1973,38.1691
[89]T. L. Hullar and S. B. Siskin, The Journal of Organic Chemistry 1970,36(1),225-228
[90]James W. Wilt, Mehboob Peeran, J. Org. Chem.1986,51(13),2618-2619
[91]Peter M. Collins, Ajay Manro, Ethel C. Opara-Mottah, et al., J. Chem. Soc., Chem. Commun. 1988,272-274
[92]Sidhaghatta D. Venkataramu, James H. Cleveland, et al., J. Org. Chem.1979,44(17), 3082-3084
[93]Lin Hai-xia, Xu Liang-heng, Huang Nai-ju, Synthetic communications 1997,27(2),303-306
[94]Tadashi Aoyama, Toshio Takido and Mitsuo Kodomari, Tetrahedron letters 2005,46, 1989-1992
[95]Shinsei Sayama, Tetsuo Onami, Synlett.2004,15,2739-2745
[96]Lawrence C.Anderson, Harold W. Pinnick, J. Org. Chem.1978,43(17),3417-3418
[97]Saburo Sugai, Takashi Kodama, Sanya Akaboshi, and Shiro Ikegami, Chem. Pharm. Bull. 1984,32(1),99-105
[98]Hakjune Rhee and Jin Yeon Kim, Bull. Korean Chem. Soc.2000,21(3),355-357
[99]B. Karimi, J. Rajabi, Journal of Molecular Catalysis A:Chemical 2005,226,165-169
[100]par Francis Barbot et Philippe Miginiac, Helvetica Chimica Acta 1979,62(5),1451-1457
[101]Christian Reichardt, Abdel-Rahman Ferwanah, et al., Liebigs Ann. Chem.1984,649-679
[102]Manish Dixit, Brajendra K. Tripathi, Akhilesh K. Tamrakar et al., Bioorganic & Medicinal Chemistry 2007,15,727-734
[103]V. G. Saraswathy and S. Sankararaman, J. Org. Chem.1994,59,4665
[104]H.Firouzabadi,N.Iranpoor and B. Karimi, Synlett.1998,739
[105]S. Samajdar, M. K. Basu, F. F. Backer and B. K. Banik, Tetrahedron Lett.2001,42,4425
[106]Sarala Naik, Rangam Gopinath, Mousumi Goswami et al., Org. Biomol. Chem.2004,2, 1670-1677
[107]Das B., Ramu R., Reddy M. R., Mahender G., Synthesis 2005,250
[108]Firouzabadi H., Iranpoor N., Amani K., Synthesis 2002,59
[1]The pophyrin Handbook Vol.1-10, Academic Press, New York,2000; The pophyrin Handbook Vol.11-20, Academic Press, New York,2004
[2]Sessler J. L., Anzenbacher P. Jr., Jursikova K., et al., Pure Appl. Chem.1998,70,2401
[3]Turner B., Shterenberg A., Kapon M., et al., Chem. Commun.2001,13
[4]Harriman A., Mehrabi M., Maiya B. G., Photochem. Photobiol. Sci.2005,4,47
[5]Namor A. F. D., Abbas I., Hammud H. H., J. Phys. Chem. B 2007,111,3098
[6]Scott T. Handy, Yanan Zhang, and Howard Bregman, J. Org. Chem.2004,69 (7), 2362-2366
[7]Haruhisa Kikuchi, Mizuki Sekiya, Yasuhiro Katou, Org. Lett.2009,11(8),1693-1695
[8]Kenza Dairi, Yuxing Yao, Michael Faley, Org. Process Res. Dev.2007,11(6),1051-1054
[9]Tsutomu Fukuda, Ei-ichi Sudo, Kozue Shimokawa, et al., Tetrahedron 2008,64,328-338
[10]Charles E. Loader, Graham H. Barnett, and Hugh J. Anderson, Can. J. Chem.1982,60, 383-389
[11]M. F. Hudson, K. M. Smith, Synthesis 1976,464-467
[12]Charles E. Loader, Hugh J. Anderson, Synthesis 1978,295-297
[13]陈金泰,陈耀焕,盛怀禹.有机化学1988,8,164-166
[14]Hermann K. Hombrecher, Gaby Horter, Synthesis 1990,389-391
[15]Franz-Peter Montforts, Ulrich M. Schwartz, Liebigs Ann. Chem.1985,2301-2303
[16]Robert M. Silverstein, Edward E. Ryskiewicz, et al., J. Org. Chem.1955,20(5),668-672
[17]Hugh J. Anderson, Can. J. Chem.1957,35,21-27
[18]Philip E. Sonnet, J. Org. Chem.1971,36(7),1005-1007
[19]Jutz C., Kirchlechner R., Siedel H. J., Chem. Ber.1969,102,2301
[20]John T. Gupton, Dale A. Krolikowski, Richard H. Yu, J. Org. Chem.1990,55(15), 4735-4740
[21]Kevin M. Smith, Michiko Miura, and Hani D. Tabba, J. Org. Chem.1983,48(24), 4779-4781
[1]J. Seyden-Penne, Reductions by the Alumino- and Borohydrides in Organic Synthesis VCH Publishers, New York,1991.
[2]H. C. Brown and R. F. McFarlin, J. Am. Chem. Soc.1956,78,752
[3]H. C. Brown and B. C. SubbaRao, J. Am. Chem. Soc.1958,80,5377
[4]H. C. Brown and A. Tsukamoto, J. Am. Chem. Soc.1964,86,1089
[5]M. Freifelder, Catalytic Hydrogenation in Organic Synthesis:Procedures and Commentary John Wiley & Sons, New York,1978
[6]Clemmensen E. Ber., Dtsch. Chem. Ges 1913,46,1837
[7]Kadam A. J., Baraskar U. K., Mane R. B., Indian J. Chem. Sect. B 2000,39B,822
[8]Kohara T., Tanaka H., Kimura K., Synthesis 2002,355
[9]Wolff L., Justus Liebigs Ann. Chem.1912,394,86
[10]Huang-Minlong, J. Am. Chem. Soc.1946,68,2487
[11]Bashore C. G.., Samardjiev I. J., J. Am. Chem. Soc.2003,125,3268
[12]Michael P. Doyle, Donald J. DeBruyn, Dale A. Kooistra, J. Am. Chem. Soc.1972,94, 3659-3661
[13]Olah G. A., Narang S. C., Meidar D., Salem G., Synthesis 1981,282
[14]George A. Olah, Takehiko Yamato, Pradeep S. Iyer, et al., J. Org. Chem.1986,51, 2826-2828
[15]Ernest L. Eliel, Mark Rerick, J. Org. Chem.1958,23,1088
[16]Abdun-Nur, A. R., Issidorides C.H., J. Org. Chem.1962,27,67-70
[17]Fleming B., Bolker H. I., Can. J. Chem.1974,52,888-893
[18]Tsunoda T., Suzuki M., Noyori R., Tetrahedron Lett.1979,48,4679-4680
[19]Home D.A., Jordan A., Tetrahedron Lett.1978,16,1357-1358
[20]N. Xavier and S. J. Arulraj, Tetrahedron 1985,41(14),2875-2878
[21]Munetaka Kunishima, Daisuke Nakata, Chem.Pharm.Bull. 2001,49(1),97-100