[3+2]- versus [4+2]-cycloaddition reactions of 3-methylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with N-substituted maleimides involving pyrrolidine-derived azomethine ylides

被引：14
作者：
Deryabina, TG
Belskaia, NP
Kodess, MI
Dehaen, W
Toppet, S
Bakulev, VA
机构：
[1] Urals State Tech Univ, Lab Technol Organ Synth, Ekaterinburg 620002, Russia
[2] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, Ekaterinburg 620219, Russia
[3] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain, Belgium
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 11期
基金：
俄罗斯基础研究基金会;
关键词：
cycloaddition; diazadienes; azomethine ylides; maleimides; pyrrolizidines;
D O I：
10.1016/j.tetlet.2005.12.130
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
3-Methylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles do not enter into [4+2]-cycloaddition reactions with male-imides to form the expected pyrrolo-pyridazines. Instead the formation of novel pyrrolo-pyridazines of type 4 takes place via a formal [3+2]-cycloaddition of initially formed pyrrolidine-derived azomethine ylides 7. The mechanism leading to the final product is discussed. (c) 2006 Elsevier Ltd. All rights reserved.
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页码：1853 / 1855
页数：3
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