Paal-Knorr Condensation for the Synthesis of Pyrrole Derivatives Under Ultrasound Irradiation

doi:10.3969/j.issn.1000-1565.2009.06.015

Abstract

Abstract: Polysubstituted pyrroles were synthesized via ultrasonic-assisted Paal-Knorr condensation of 1,4-diketone with aromatic amines at room temperature. Compared with conventional heating method, the ultrasonic-assisted reaction showed certain practical value for it's higher yield, shorter reaction time, mild reaction condition, simple procedure and so on.

Key words: ultrasound irradiation, Paal-Knorr reaction, 1.4-diketone, aromatic amine, polysubstituted pyrroles

CLC Number:

O621.3

ZHANG Shu-wen,ZHANG Xing,WEI Bao-jun,HAO Peng-peng. Paal-Knorr Condensation for the Synthesis of Pyrrole Derivatives Under Ultrasound Irradiation[J]. Journal of Hebei University (Natural Science Edition), 2009, 29(6): 618-622.

References

[1] 张娟, 范晓东, 刘毅锋, 李华, ZHANG Juan, FAN Xiao-dong, LIU Yi-feng, LI Hua. Paal-Knorr缩合法合成N-烷氧羰基-2, 5-二甲基吡咯 [J]. 现代化工 2006.doi:10.3321/j.issn:0253-4320.2006.11.012
[2] 李记太, 臧洪俊, LI Ji-tai, ZANG Hong-jun. 超声波应用于有机合成方面的新进展 [J]. 河北大学学报（自然科学版） 2000.doi:10.3969/j.issn.1000-1565.2000.01.026
[3] 杜玉英, 田福利, 赵文芝, 方利, Du Yuying, Tian Fuli, Zhao Wenzhi, Fang Li. 利用Paal-Knorr反应在无催化剂和溶剂条件下合成吡咯衍生物 [J]. 化学通报（印刷版） 2006.doi:10.3969/j.issn.0441-3776.2006.04.025
[4] BOULTON A J, MCKILLOP A. Comprehensive heterocyclic chemistry [M]. Oxford:pergamon Press 1984.
[5] JONES R A. Pyrroles Part II:the synthesis, reactivity and physical properties of substituted pyrroles [M]. New York:wiley 1992.
[6] SEREF D, AHMET C, NURI K. Synthesis and antibacterial activities of some 1-[2-(substituted pyrroL-1-yl)ethyl]-2-methyl-5-nitroimidazole derivatives [J]. European Journal of Medicinal Chemistry 1999, 34.
[7] ALMERICO A M, DIANA P, BARRAJA P. Glycosidopyrroles part 1:acyclic derivatives:1-(2-hydroxyethoxy) methylpyrroles as potential anti-viral agents [J]. Farmaco 1998, 53.
[8] Harrak Y, Rosell G, Daidone G, Plescia S, Schillaci D, Pujol MD. Synthesis and biological activity of new anti-inflammatory compounds containing the 1, 4-benzodioxine and/or pyrrole system. [J]. Bioorganic and medicinal chemistry 2007, 14(14).
[9] Mariangela Biava, Giulio Cesare Porretta, Delia Deidda, Raffaello Pompei, Andrea Tafi, Fabrizio Manetti. Antimycobacterial compounds. New pyrrole derivatives of BM212 [J]. Bioorganic and medicinal chemistry 2004, 6(6).
[10] FUNISS B S, HANNAFORD A J, SMITH W G. Vogel's textbook of practical organic chemistry [M]. London:Longmann Group UK Limited 1989.
[11] Bimal K.Banik, Indrani Banik, Mercy Renteria, Swapan K.Dasgupta. A straightforward highly efficient Paal-Knorr synthesis of pyrroles [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2005, 15(15).
[12] Chen JX, Wu HY, Zheng ZG, Jin C, Zhang XX, Su WK. An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)(3) under solvent-free conditions [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2006, 30(30).
[13] Sreekumar R., Padmakumar R.. Simple, efficient and convenient synthesis of pyrroles and pyrazoles using zeolites. [J]. Synthetic Communications 1998, 9(9).
[14] H.Surya, Prakash Rao, S.Jothilingam. One-pot synthesis of pyrrole derivatives from (E)-1, 4-diaryl-2-butene-1, 4-diones [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2001, 37(37).
[15] Bo Wang, Yanlong Gu, Cheng Luo, Tao Yang, Liming Yang, Jishuan Suo. Pyrrole synthesis in ionic liquids by Paal–Knorr condensation under mild conditions [J]. Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry 2004, 17(17).
[16] 李述文, 范如霖. 实用有机化学手册 [M]. 上海:上海科学技术出版社 1981.
[17] ZHANG Shuwen, WEI Baojun, HAO Pengpeng. Synthesis and characterization of N, N′-substituted bis (3-acetyl-2-methyl-5-p-methoxyphenyl) pyrroles [J]. Chmical Journal on Internet 2007, 9.
[18] 李葆. 多取代吡咯的合成及其性质（Ⅰ） [J]. 1985.