摘要
1, 2, 3-三唑和吡唑结构单元具有广泛生物活性,受到有机合成、药物合成等方面专家的日趋重视。吲哚作为一类非常重要的杂环化合物,在医药化学、农业化学和材料科学等领域有着非常广泛的应用。目前,3-取代吲哚化合物尤其是双吲哚甲烷和β-吲哚酮的研究已成为吲哚化学中最活跃的领域之一。
室温离子液体一般是由有机阳离子和无机阴离子构成的、在室温或近于室温下呈液态的物质。离子液体以其独特的物理化学性质,如不挥发性、热稳定性、良好的导电性等,近年来在催化反应、有机合成以及电化学等领域得到了广泛的应用,是国际上研究的热点领域之一。鉴于此,本文选用Br?nsted酸性离子液体作为催化剂催化合成一系列含吡唑和1, 2, 3-三唑类杂环3-取代吲哚衍生物,并对反应条件进行了优化。本论文分为以下两部分:
第一部分为文献综述,针对离子液体、双吲哚甲烷和β-吲哚酮合成及应用进行了较为系统的阐述。
第二部分为实验部分,主要工作分为四个部分:
一.Br?nsted酸性离子液体催化吲哚化合物和查尔酮反应合成β-吲哚酮
二.Br?nsted酸性离子液体[Sbmim][HSO4]催化吲哚化合物和α,β-不饱和羰基化合物反应合成三唑杂环基β-吲哚酮
三.Br?nsted酸性离子液体[BSbbt][HSO4]催化吲哚化合物和3-甲基-1-苯基-4-芳亚甲基-5-吡唑啉酮的Michael加成反应
四.Br?nsted酸性离子液体[PyNCH2CO2H][HSO4]催化吲哚化合物和1, 2, 3-三唑醛、吡唑醛反应合成双吲哚甲烷衍生物产物结构经1H NMR、MS、IR和元素分析得到确证。
1,2,3-triazole and pyrazole structural units are so biologically active that experts from the areas of orgaic synthesis and medical synthesis pay more attetion to them. Indole as an important kind of heterocyclic compounds is applied widely in medical chemistry, agricultural chemistry, material science and so on. Recently, 3-substituted indoles especiallyβ-indolylketones and bis-indolylmethanes have been one of the most active areas in indole chemistry.
Ionic liquids entirely composed of cations and anions were liquid in room temperature. They have recently been attracted much attention in organic synthesis, catalysis and electrochemistry due to their unique properties such as nonvolatile, high thermal stability and good conducting ability. In view of this, this article used acidic ionic liquids as catalysts to synthesize a series of 3-substituted indole derivatives containing pyrazolyl or 1,2,3-triazolyl and reaction conditions were optimized.
This thesis consists of two major parts:
The first part is about literature review. The progress introduced the ionic liquid, bis-indolylmethane andβ-indolylketones.
The second part is about experimental content. Major work as follows:
1. The systhesis ofβ-indolylketones by the reaction of indole and chalcone using br?nsted acidic ionic liquid as catalyst.
2. The systhesis ofβ-indolylketones containing 1,2,3-triazolyl by the reaction of indole andα,β-unsaturated carbonyl compounds using br?nsted acidic ionic liquid [Sbmim][HSO4] as catalyst.
3. The Michael addition reaction of indoles to 4-arylmethyl-3- methyl-1-phenylpyrazol-5-one catalyzed br?nsted acidic ionic liquid [BSbbt][HSO4].
4. The systhesis of bis-indolylmethanes containing 1,2,3-triazolyl or pyrazolyl by the reaction of indole and 4-formyl-1,2,3-triazol or 4-formylpyrazole using br?nsted acidic ionic liquid [PyNCH2CO2H][HSO4] as catalyst.
The structures of new compounds were confirmed on the basis of 1H NMR, MS, IR spectrum and element analysis.
引文
[1] Abramovitch, R. A.; Spenser, I. D. Advances in Heterocyclic Chemistry[M]: Academic Press: New York. 1964, 3, 79.
[2] Takeuchi, T.; Nitta, K.; Tanaka, N. Antitumor Natural Produce[M]; Japan Scientific Press: Tokyo. 1989, 1-55.
[3] Abel, E.; De Wall, S. L.; Edwards, W. B.; Lalitha, S.; Covey, D. F.; Gokel, G. W. Formation of Stable Vesicles from N- or 3-Alkylindoles: Possible Evidence for Tryptophan as a Membrane Anchor in Proteins[J]. J. Org. Chem. 2000, 65, 5901-5905.
[4] Austin, J. F.; Macmillan, D. W. C. Enantioselective Organocatalytic Indole Alkylations. Design of a New and Highly Effective Chiral Amine for Iminium Catalysis[J]. J. Am. Chem. Soc. 2002, 124, 1172-1173.
[5] Zhan, Z. P.; Yan, G. R. F.; Lan, G. K. Samarium triiodide-catalyzed conjugate addition of indoles with electron-deficient olefins[J]. Tetrahedron Lett. 2005, 46, 3859-3861.
[6] AURIA, M. Photochemical synthesis of diindolylmethanes[J]. Tetrahedron. 1991, 47, 9225-9227.
[7] Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L.T.; Weaver, K. J.; Forbes, D. C. ; J. H. D, Jr. Novel br?nsted acidic ionic liquids and their use as dual solvent Catalysts[J]. J. Am. Chem. Soc. 2002, 124, 5962-5963.
[8] Chritopher, J. B.; Duncan, W. B.; Kenneth, R. S. Liquid-crystalline ionic liquid[J]. Chem. Commun. 1996, 14, 1625-1628.
[9] Tait, S.; Osteryoung, R. A. Infrared study of ambient-temperature chloroluminate as a function of melt acidity[J]. Inorg. Chem.. 1984, 23, 4352-4360.
[10] Hurley, F. H.; Wier, T. P. Electrodeposition of metals from fused quanternary ammonium[J]. Salts. Electrochemical. Society. 1951, 98, 203-208.
[11] Koch, V. R.; Mileer, L. L.; Osteryoung, R. A. Electoinitiated Friedel-Crafts translkylations in a room temperature molten-salts medium[J]. J. Am. Chem. Soc. 1976, 98, 5277-5280.
[12] Wilkes, J. S.; Levisky, J. A.; Wilson, R.. A.; Hussey, C. L. Alkyl-limidazoliumchloroalumin-ate melts, a new class of room temperature ionic liquids for electrochemistry spectroscopy and systhesis[J]. Inorg. Chem..1982, 21, 1263-1268.
[13] Hussey, C. L. Room temperature haloaluminate ionic liquids. Novel solvents for transition metal solution chemistry[J]. Pure. Appl. Chem. 1988, 60, 1763-1772.
[14] Wilkes, J. S.; Zaworotko, M. J. Air and water stable 1-ethyl-3-methylimidaxzolium based ionic liquid[J]. J. Chem. Soc. Commun. 1992, 9, 965-967.
[15] Macfarlane, D. R.; Pringle, J. M.; Johansson, K. M.; Forsyth, S. A.; Forsyth, M. Lewis base ionic liquids[J]. Chem. Commun. 2006, 1905-1917.
[16] Li, S.; Lin, Y.; Xie, H.; Zhang, S.; Xu, J. Br?nsted Guanidine Acid?Base Ionic Liquids: Novel Reaction Media for the Palladium-Catalyzed Heck Reaction[J]. Org. Lett. 2006, 8, 391-393.
[17] Egashiraa, M.; Drib, D. A. Novel preparation of nanocomposite polymer electrolyte and its application to lithium polymer batteries[J]. J. Power. Sources. 2004, 138, 245-252.
[18] Sato, T.; Masuda, G.; Takagi, K. Electrochemical properties of novel ionic liquids for electric double layer capacitor applications[J]. Electrochim. Acta. 2004, 49, 3603-3611.
[19] Fukumoto, K.; Yoshizawa, M.; Ohno, H. Room Temperature Ionic Liquids from 20 Natural Amino Acids[J]. J. Am. Chem. Soc. 2005, 127, 2398-2399.
[20] Varma, R. S.; Namboodiri, V. V. An expeditious solvent-free route to ionic liquids using microwaves[J]. Chem. Commun. 2001, 643-644.
[21] Lall, S.; Mancheno, D.; Castro, S. V. A new category of room temperature ionic liquid based on polyammonium salts[J]. Chem. Commun. 2000, 2413-2414.
[22] Jin, C.; Twamley, B.; Shreeve, J. M. Synthesis, structures and spectroelectrochemistry of methyl-substituted bis(?5-indenyl)iron(II) complexes[J]. Organometallics. 2005, 24, 3018-3026.
[23] Tao, G.; He, L.; Sun, N.; Kou, Y. New generation ionic liquids: cations derived from amino acids[J]. Chem. Commun. 2005, 3562-3564.
[24] Tang, J.; Sun, W.; Tang, H.; Radosz, M.; Shen, Y. Enhanced CO2 Absorption of Poly(ionic liquid)s[J]. Macromolecules. 2005, 38, 2037-2039.
[25] Wang, Y. Y.; Jiang, D.; Dai, L. Y. Novel Br?nsted acidic ionic liquids based on benzimidazolium cation: Synthesis and catalyzed acetalization of aromatic aldehydes with diols[J]. Catal. Commun. 2008, 9, 2475–2480.
[26] Abbott, A. P.; Capper, G.; Davies, D. L.; Rasheed, R. Ionic Liquids Based upon Metal Halide/Substituted Quaternary Ammonium Salt Mixtures[J]. Inorg. Chem. 2004, 43, 3447-3452.
[27] Chiappe, C.; Leandri, E.; Pieraccini, D. Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent/solvent[J]. Chem. Commun. 2004, 2536-2537.
[28] Huang, L.; Zhai, M.; Peng, J.; Xu, L.; Li, J.; Wei, G. Synthesis of room temperature ionic liquids from carboxymethylated chitosan[J]. Carbohyd. Polym. 2008, 71, 690-693.
[29] Pernak, J.; Feder-Kubis, J. Synthesis and Properties of Chiral Ammonium-Based Ionic Liquids[J]. Chem. Eur. J. 2005, 11, 4441-4449.
[30] Mirzaei, Y. R.; Twamley, B.; Shreeve, J. M. Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation of Quaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium Salts Leading to Ionic Liquids[J]. J. Org. Chem. 2002, 67, 9340-9345.
[31] Macfarlane, D.R.; Golding, J.; Forsyth, S.; Forsyth, M.; Deacom, G. B. Low viscosity ionic liquids based on organic salts of the dicyanamide anion[J]. Chem. Commun. 2001, 1430-1431.
[32]侯亚伟.功能化离子液体的制备、性能及应用的研究[D],博士研究生学位论文,华东师范大学,上海,2009.
[33] Dai, L.; Yu, S.; He, M. Novel room temperature inorganic ionic liquid[J]. Eur. J. Inorg. Chem. 2004, 2, 237-241.
[34]卢泽湘,袁霞.咪唑类离子液体的合成与光谱表征[J].化学世界. 2005, 2, 148-150.
[35] Wasserscheid, P.; Keim, W. Ionic liquids-newl solutions for transition metal catalysis[J]. Angew. Chem. Int. Ed.. 2000, 39, 3772-3789.
[36] Wasserscheid, P.; Bolm, C. Synthesis and properties of ionic liquids derived from the chiralpool[J]. Chem. Commun. 2002, 3, 200-201.
[37] Branco, L. C.; Rosa, J. N.; Moura Rarnos, J. J.; Alfons, C. A. M. Preparation and Characterization of New Room Temperature Ionic Liquids[J]. Chem. Eur. J. 2002, 8, 3671-3677.
[38] Ngo, H. L.; Lecompte, K.; Hargens, L. Thermal properties of imidazolium ionic liquid[J]. Thermochim. Acta. 2003, 357, 97-102.
[39]王要令,徐军,陈宜良,宗旭.酸性离子液体研究新进展[J].山东化工. 2007, 36, 9-17.
[40]李雪辉,李榕,陈学伟,王芙蓉,王乐夫.碱性离子液体研究进展[J].工业催化. 2007, 15, 1-5.
[41]郜蕾, SO3H-功能化离子液体的合成及催化性能研究[D].硕士研究生学位论文,大连理工大学,大连,2009.
[42] Bonhote, P.; Dias, A. P.; Papageorgious, N.; Kalyanasundaram, K.; Gratzel, M. Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts[J]. Inorg.. Chem. 1996, 35, 1168-1178.
[43]杨雅立,王晓化,寇元.离子液体的酸性测定及其催化的异丁烷/丁烯烷基化反应[J].催化学报. 2004, 25, 60-64.
[44] Muldoon, M. J.; Gordon, C. M.; Dunk, I. R. Investtigation of solvent-solute interaction in room temperature ionic liquids using solvatochromic dyes[J]. J. Chem. Soc. Perkin Tran2. 2001, 4, 433-435.
[45] Baker, S. N.; Kane, M. A.; Bright, F. V. The Cybotactic region surrounding fluorescent probes dissolved in 1-butyl-3-methylimidazoulium hexafluoro phosphate: effects of temperature and added carbon dioxide[J]. J.Phys. Chem.B. 2001, 105, 9663-9668.
[46] Pool, S. K.; Poole, C. F. Chemometric evaluation of solvent properties of liquids organic salts[J]. Analyst. 1995, 117, 1508-1513.
[47]石家华,孙逊,杨春和.离子液体研究进展[J].化学通报. 2002, 4, 243-250.
[48] Dupont, J.; Consorti, C. S.; Suarez, P. A. Z. Preparation of 1-butyl-3-metylimidazolium-basedroom temperature ionic liquid[J]. Organic.Synthesis. 2002, 79, 236-237.
[49] Bhushan, M. K.; Geetal, R. Microwave-assisted synthesis of room temperature ionic liquid precursor in closed vessel[J]. Org. Process Res. Deve. 2002, 6, 826-828.
[50] Leveque, J. M.; Luche, J. L.; Petier, C. An improved preparation of ionic liquids by ultrasound[J]. Green Chem. 2002, 4, 357-360.
[51] Moulton, R. Electrochemical process for producing ionic liquids: US.0094380[P]. 2003.
[52] Stepnowski, P.; Zaleska, A. Comparision of different advanced oxidation processes for the degradation of room temperature ionic liquids[J]. J. Photoch. Photobi.A. 2005, 170, 45-50.
[53] Yang, H. Z.; Gu, Y. L.; Deng, Y. Q. Electrochemical activation of carbondioxide in ionic liquid: synthesis of cyclic carbonates at mild reaction conditions[J]. Chem. Commun. 2002, 3, 274-275.
[54] Copper, E. R.; Andrews, C. D.; Wheatley, P. S. A new methodology for zeolite analogue synthesis using ionic liquids as solvent and template[J]. Studies in Surface Science and Catalysis. 2005, 158, 247-254.
[55] Huddlestou, J. G.; Willauer, H. D.; Rogers, R. D. Room temperature ionic liquid as novel media for clean liquid-liquid extraction[J]. Chem. Commun. 1998, 1765-1766.
[56] Visser, A. E.; Swatloski, R. P.; Reichert, W. M.; Mayton, R.; Sheff, S.; Wierzbicki, A.; Davis, J. H.; Rogers, R. D. Task-special ionic liquids for the extraction of metal ions from aqueous solutions[J]. Chem. Commun. 2001, 135-136.
[57] Bosman, A.; Datesevich, L.; Jess, A.; Lauter, A.; Schmitz, C.; Wasserscheid, P. Deep desulfurization of diesel fuel by extraction with ionic liquids[J]. Chem. Commun. 2001, 2494-2495.
[58] Welton, T. Room-Temperature Ionic Liquids. Solvents for Synthesis and Catalysis[J]. Chem. Rev. 1999, 99, 2071-2084.
[59] Sheldon, R. Catalytic reactions in ionic liquids[J]. Chem. Commun. 2001, 2399-2407.
[60] Prvulescu, V. I.; Hardacre, C. Catalysis in Ionic Liquids[J]. Chem. Rev. 2007, 107,
[61] Peng, J.; Deng, Y. Ionic liquids catalyzad Biginelli reaction under solvent-free conditions[J]. Tetrahedron Lett. 2001, 42, 5917-5919.
[62] Lee, J. K.; Kim, D. C.; Song, C. E.; Lee, S. Thermal Behaviors of ionic liquids under microwave irradiation and their application on microwave-assisted catalytic Beckmann Rearrangement of Ketoximes[J]. Synth. Commun. 2003, 33, 2301-2307.
[63] Dell,Anna, M. M.; Gallo, V.; Mastrorilli, P.; Nobile, F. C.; Ramanazzi, G.; Suranna, G. P. Metal catalysed Michael additions in ionic liquids[J]. Chem. Commun. 2002, 434-435.
[64] Peng, J.; Shi, F.; Deng, Y. Highly selective and green aqueous-ionic liquid biphasic hydroxylation of benzene to phenol with peroxide[J]. Green. Chem. 2003, 5, 224-226.
[65] Auria, M. Photochemical synthesis of diindolylmethanes[J]. Tetrahedron. 1991, 47, 9225-9227.
[66] Harrington, P. E.; Kerr, M. A. Reaction of Indoles with Electron Deficient Olefins Catalyzed by Yb(OTf)3·3H2O[J]. Synlett. 1996, 1047-1048.
[67] Shi, M.; Cui, S.C.; Li, Q.J. Zirconium triflate-catalyzed reactions of indole, 1-methylindole, and pyrrole withα,β-unsaturated ketone [J]. Tetrahedron. 2004, 60, 6679-6684.
[68] Bartoli, G.; Bartolacci, M. The Michael Addition of Indoles toα,β-Unsaturated Ketones Catalyzed by CeCl3·7H2O-NaI Combination Supported on Silica Gel [J]. J. Org. Chem. 2003, 68, 4594-4597.
[69] Li, D. P.; XIAO, W. J. Organocatalytic C3-selective Friedel-Crafts alkylations of indoles withα,β-unsaturated ketones[J]. Chem. Commun. 2006, 7, 799-801.
[70] Yadav, J.S.; Reddy, B.V.S.; Baishya, G.; Reddy, K.V.; Narsaiah, A.V. Conjugate addition of indoles toα,β-unsaturated ketones using Cu(OTf)2 immobilized in ionic liquids[J]. Tetrahedron. 2005, 61, 9541-9544.
[71] Ji, S. J.; Wang, S. Y. An expeditious synthesis of b-indolylketones catalyzed by p-toluene- -sulfonic acid (PTSA) using ultrasonic irradiation[J]. Ultrason. Sonochem. 2005, 12. 339—343.
[72] Vanderlaag, K.; Samudio I.; Burghardt, R.; Barhoumi, R.; Safe, S. Inhibition of breast cancercell growth and induction of cell death by 1,1-bis(3'-indolyl)methane (DIM) and 5,5'-dibromoDIM[J]. Cancer Lett. 2006, 236, 198–212.
[73] Magesh, C. J.; Nagarajan, R.; Karthik, M.; Perumal, P. T. Synthesis and characterization of bis(indolyl)methanes, tris(indolyl)methanes and new diindolylcarbazolylmethanes mediated by Zeokarb-225, a novel, recyclable, eco-benign heterogenous catalyst[J]. Appl. Catal. A: Gen. 2004, 266, 1–10.
[74] Kamble, V. T.; Kadam, K. R.; Joshi, N. S.; Muley, D. B. HClO4–SiO2 as a novel and recyclable catalyst for the synthesis of bis-indolylmethanes and bis-indolylglycoconjugates[J]. Catal. Commun. 2007, 8, 498–502.
[75] Chen, D.; Yu, L.; Wang, P. G. Lewis acid–catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones[J]. Tetrahedron. Lett. 1996, 37, 4467-4470.
[76] Bandgar, B. P.; Shaikh, K. A. Molecular iodinecatalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions[J]. Tetrahedron. Lett. 2003, 44, 1959-1961.
[77] Manas, C.; Nandita, G.; Ramkrishna, B.; Yoshihiro, H. Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A[J]. Tetrahedron Lett. 2002, 43, 4075–4078.
[78] Magesh, C. J.; Nagarajan, R.; Perumal, P. T. Synthesis and characterization of bis(indolyl)methanes, tris(indolyl)methanes and new diindolylcarbazolylmethanes mediated by Zeokarb-225, a novel, recyclable, eco-benign heterogenous catalyst[J]. Appl. Catal. A:General. 2004, 266,1-10.
[79] Sharma, G. V. M.; Reddy, J. J.; Lakshmi, P. S. A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine[J]. Tetrahedron Lett. 2004, 45, 7729-7732.
[80] Li, J. T.; Dai, H. G.; Xu, W. Z. An e?cient and practical synthesis of bis(indolyl)methanes catalyzed by aminosulfonic acid under ultrasound[J]. Ultrason. Sonochem. 2006, 13, 24-27.
[81] Zhan, Z. P.; Yang, R. F.; Lang, K. Samarium triiodide-catalyzed conjugate addition ofindoles with electron-deficient olefins[J]. Tetrahedron Lett. 2005, 46, 3849–3852.
[82] Szmuszkovicz, J. The Reaction of Substituted Indoles with Methyl Vinyl Ketone. New Synthesis of 2-Methylcarbazole[J]. J. Am. Chem. Soc. 1957, 79 , 2819-2821.
[83] Evars, D.A.; Fandrick, K.R.; Song, H.J. Enantioselective Friedel-Crafts Alkylations ofα,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Bis(oxazolinyl)pyridine-Scandium(III) Triflate Complexes[J]. J. Am. Chem. Soc. 2005, 127 , 8942-8943.
[84] Zhou, J.; Ye, M.C.; Huang, Z.Z.; Tag, Y. Controllable Enantioselective Friedel-Crafts Reaction1 between Indoles and Alkylidene Malonates Catalyzed by Pseudo-C3-Symmetric Trisoxazoline Copper(II) Complexes[J]. J. Org. Chem. 2004, 69 , 1309-1320.
[85] Yang, Q. W.; Wei, Z. J.; Xing, H. B.; Ren, Q. L. Br?nsted acidic ionic liquids as novel catalysts for the hydrolyzation of soybean iso?avone glycosides[J]. Catal. Commun. 2008, 9, 1307-1311.
[86] Liu, X.; Zhou, J. X.; Guo, X. W.; Liu, M.; Ma, X. L.; Song, C. S.; Wang, C. SO3H-Functionalized Ionic Liquids for Selective Alkylation of p-Cresol with tert-Butanol[J]. Ind. Eng. Chem. Res. 2008, 47, 5298-5303.
[87]李在国,汪清民,黄君珉.有机中间体制备,第2版[M].北京:化学工业出版社, 2000, 51.
[88]刘方明,王宝雷,李燕萍. 1, 3-偶极环加成合成新型含2-苯基-1, 2, 3-三唑基-1, 5-并硫氮杂噁二唑并合衍生物[J].高等学校化学学报. 2002, 23, 2097-2101.
[89]胡亮,黄培池. 5-甲基-1-芳基-1,2,3-三唑衍生物的合成研究[J].化工技术与开发. 2006, 35, 7-9.
[90]张自义,刘莹,杨世琰. 5-醛胺基-1-芳基-1,2,3-连三唑[2,4-d]-嘧啶-4-酮类衍生物合成和抗菌性能[J].高等学校化学学报. 1991, 12, 1344-1348.
[91] Mirzaei, Y. R.; Twamley, B.; Shreeve, J. M. Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation of Quaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium Salts Leading to Ionic Liquids[J]. J. Org. Chem. 2002, 27, 9340-9345.
[92] Visser, A. E.; Holbrey, J. D.; Rogers, R. D. Hydrophobic ionic liquids incorporatingN-alkylisoquinolinium cations and their utilization in liquid–liquid separations[J]. Chem.Commun. 2001, 2484-2485.
[93] Jayamma, Y.; Reddy, V. M. Synthesis and biological activities of 1-[(3,4-dihydro-3-oxo-2h- 1,4-benzoxazin-2-yl) acetyl]-3,4-disubstituted pyrazoles and 3- methyl-pyrazoliones[J]. Indian J . Pharm. Sci . 1994, 56, 132.
[94] Villemin, D.; Labiad, B. Clay Catalysis: Dry Condensation of Tetronic Acid with Aldehydes under Microwave Irradiation. Synthesis of 3-(Arylmethylene)-2,4-(3H, 5H) Furandiones[J]. Synth. Commun. 1990, 20, 3207-3212.
[95] Hamama, W. S. Pyrazolones as versatile precursors for the sythesis of fused and binary heterocycles[J]. Synth. Commun. 2001, 31, 1335-1345.
[96] Li, X. L.; Wang, Y. M.; Du, D. M.; Wen, Z.; Xiong, G. X.; Meng, J. B. Solide state reactions of nitrogenous heterocylic compounds[J]. Science in China(Series B), 1997, 40, 270-277.
[97]张素梅.功能化离子液体的制备、性能及应用的研究[D],博士研究生学位论文,华东师范大学,上海,2005.
[98]白银娟,李敏,路军,王振军,史真.无溶剂无催化剂微波促进下1-苯基-3-甲基-5-吡唑啉酮与芳醛的反应研究[J].有机化学. 2004, 24, 616-620.
[99] Kamal, A.; Qureshia, A. Synthesis of some substituted diindoly methanes in aqueous medium at room temperature[J]. Tetrahedron . 1963, 19, 123-125.
[100] Wolf, J. F.; Rathnlna, T. L.; Sleevi, M. C. Synthesis and anticonvulsant activity of some new 2-substituted-3-aryl-4(3H)-quinazolinones[J]. J. Med. Chem. 1990, 33, 161-163.
[101] Wang, Z. M.; Wang, C. N.; Bao, W. L.; Ying, T. K. Task-specific ionic liquids as efficient green and recyclable reagents and solvents for oxidation of olefins[J]. J. Chem. Research. 2005, 388-390.
[102]李在国,汪清民,黄君珉.有机中间体制备,第2版[M].北京:化学工业出版社, 2000, pp.153-154.
[103]刘方明,曹玲华. 2-苯基接三唑衍生物的合成研究[J].新疆大学学报(自然科学版), 1993, 10, 70-74.
