The birch reduction of 3-substituted pyrroles

被引：24

作者：

Donohoe, TJ ^{[1
]}

Guyo, PM ^{[1
]}

Harji, RR ^{[1
]}

Helliwell, M ^{[1
]}

Cousins, RPC ^{[1
]}

机构：

[1] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(98)00362-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Birch reduction of electron-deficient 3-substituted pyrroles is described. Use of a reductive alkylation procedure involving sodium metal in liquid ammonia gave good yields of 4-alkyl-2-pyrrolines. The identity of these products was proven by an X-ray structure of a crystalline derivative. Moreover, the pyrroles used in this study could be readily prepared by reaction of TOSMIC with acrylic amides and esters and, once the reduction was complete, the ester activating group could be easily removed to yield the corresponding N-protected beta-proline derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3075 / 3078

页数：4

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