Heck arylations of N-acyl-3-pyrroline and N-acyl-1,2,5,6-tetrahydropyridine with aryldiazonium salts.: Short syntheses of aryl γ- and δ-lactams, baclofen, homobaclofen and analogues

被引：40

作者：

Carpes, MJS ^{[1
]}

Correia, CRD ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

基金：

巴西圣保罗研究基金会;

关键词：

D O I：

10.1016/S0040-4039(01)02267-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heck arylation of N-acyl-3-pyrrolines and an N-acyl-tetrahydropyridine with aryldiazonium tetrafluoroborates under phosphine-free conditions proceeded smoothly to give alpha-hydroxycarbamates (hemiaminals) or alpha-alkoxycarbamates which were oxidized to the desired gamma- and delta-lactams. Acidic hydrolysis of the gamma-lactams produced a series of arylated GABA derivatives, including baclofen, a useful therapeutic drug. in only three steps with ail overall yield of 63 76%, Starting from N-acyl-tetrahydropyridine, aryl-delta-lactams and higher homologues of baclofen can be obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：741 / 744

页数：4

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