Copper-catalyzed one-pot N-alkenylation and N-alkylation of amides: an efficient synthesis of substituted 2,3-dihydropyrroles

被引:27
作者
Zhou, Xiaobo
Zhang, Huimin
Yuan, Jiwei
Mai, Lugen
Li, Yanzhong
机构
[1] E China Normal Univ, Dept Chem, Shanghai 200062, Peoples R China
[2] E China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
基金
中国国家自然科学基金;
关键词
copper catalyst; N-alkenylation; N-alkylation; amides; dihydropyrroles;
D O I
10.1016/j.tetlet.2007.07.221
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel copper-catalyzed synthesis of substituted 2,3-dihydropyrroles via one-pot N-alkenylation and N-alkylation of amides with 1.4-diiodobut-1-ene derivatives has been developed. The reactions proceed in good to high yields using CuI as the catalyst, K2CO3 as the base, and rac-trans-N,N'-dimethylcycloliexane-1,2-diamine as the ligand. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7236 / 7239
页数:4
相关论文
共 53 条
[1]   Synthesis and screening for antiacetylcholinesterase activity of (1-benzyl-4-oxopiperidin-3-ylidene)methylindoles and -pyrroles related to donepezil [J].
Andreani, A ;
Cavalli, A ;
Granaiola, M ;
Guardigli, M ;
Leoni, A ;
Locatelli, A ;
Morigi, R ;
Rambaldi, M ;
Recanatini, M ;
Roda, A .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (23) :4011-4014
[2]   Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles [J].
Antilla, JC ;
Baskin, JM ;
Barder, TE ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5578-5587
[3]   CHEMOSELECTIVE FUNCTIONALIZATION OF ZIRCONACYCLOPENTENES [J].
AOYAGI, K ;
KASAI, K ;
KONDAKOV, DY ;
HARA, R ;
SUZUKI, N ;
TAKAHASHI, T .
INORGANICA CHIMICA ACTA, 1994, 220 (1-2) :319-326
[4]  
Bailly C., 2004, CURR MED CHEM ANTICA, V4, P364
[5]   Pyrrole syntheses by multicomponent coupling reactions [J].
Balme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241
[6]   Design, synthesis, and biological evaluation of hybrid molecules containing α-methylene-γ-butyrolactones and polypyrrole minor groove binders [J].
Baraldi, PG ;
Nunez, MD ;
Tabrizi, MA ;
De Clercq, E ;
Balzarini, J ;
Bermejo, J ;
Estévez, F ;
Romagnoli, R .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (11) :2877-2886
[7]   A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2-c]quinolines [J].
Batey, RA ;
Simoncic, PD ;
Lin, D ;
Smyj, RP ;
Lough, AJ .
CHEMICAL COMMUNICATIONS, 1999, (07) :651-652
[8]   Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2006, 62 (31) :7213-7256
[9]   2,5-Dihydropyrrole derivatives as enantiomerically enriched building blocks: Synthesis of the Geissman-Waiss lactone and polyhydroxylated pyrrolidines [J].
Cinquin, C ;
Bortolussi, M ;
Bloch, R .
TETRAHEDRON-ASYMMETRY, 1996, 7 (11) :3327-3332
[10]   Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950 [J].
Coleman, RS ;
Liu, PH .
ORGANIC LETTERS, 2004, 6 (04) :577-580