Efficient synthesis of 5,6,7-trisubstituted 1H-pyrrolizines

被引：82

作者：

Yavari, I ^{[1
]}

Adib, M ^{[1
]}

机构：

[1] Univ Taarbiat Modarres, Dept Chem, Tehran, Iran

来源：

TETRAHEDRON | 2001年 / 57卷 / 27期

关键词：

5,6,7-trisubstituted 1H-pyrrolizines; 2-pyrrolylglyoxalate; N-benzyl-2-pyrrolylglyoxamate;

D O I：

10.1016/S0040-4020(01)00525-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and strong NH-acids, such as 2-pyrrolylglyoxalate or N-benzyl-2-pyrrolylglyoxamate. These phosphoranes undergo a smooth intramolecular Wittig reaction in boiling toluene to produce 5,6,7-trisubstituted 1H-pyrrolizine derivatives in quantitative yields. Dynamic NMR effects are observed in the H-1 NMR spectra of stabilized ylides 6a and 6d (DeltaG(not equal)=67.6 and 69.5 kJ mol(-1), respectively) and are attributed to restricted rotation around the carbon-carbon partial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl group. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5873 / 5878

页数：6

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