A direct link between the Passerini reaction and α-lactams

被引：15

作者：

Lengyel, I

Cesare, V

Taldone, T

机构：

[1] St Johns Univ, Dept Chem, Jamaica, NY 11439 USA

[2] St Johns Univ, Dept Pharmaceut Sci, Jamaica, NY 11439 USA

来源：

TETRAHEDRON | 2004年 / 60卷 / 05期

关键词：

aziridinones; maleic anhydride; mono- and dicarboxylic acids; nucleophilic substitution; Passerini reaction;

D O I：

10.1016/j.tet.2003.11.067

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Lactams (aziridinones) can function to replace two of the three reactants, the oxo-compound and the isonitrile, in the Passerini reaction. Four alpha-lactams (5a-d) were reacted with mono- and dicarboxylic acids of positive pK(a) values to give 2-acyloxycarboxamides (4) and bis-2-acyloxycarboxamide products 12 and 13, respectively. The same compounds were also prepared via the Passerini reaction. Acids with a negative pK(a) decarbonylate alpha-lactams to give immonium salts. The main path of the reaction depends on the pK(a) of the acid component, the reactivity of the alpha-lactam, and the reaction conditions. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1107 / 1124

页数：18

共 51 条

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[2]

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