THE MECHANISMS OF HYDROLYSIS OF THE GAMMA-LACTAM ISATIN AND ITS DERIVATIVES

被引：32

作者：

CASEY, LA

GALT, R

PAGE, MI

机构：

[1] UNIV HUDDERSFIELD,DEPT CHEM SCI,HUDDERSFIELD HD1 3DH,ENGLAND

[2] ICI PLC,DIV PHARMACEUT,MACCLESFIELD SK10 4TG,CHESHIRE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1993年 / 01期

关键词：

D O I：

10.1039/p29930000023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pH dependences of the rates of hydrolysis of isatin its N-carboxymethyl derivative and its 5-nitro substituted analogues exhibit a complex behaviour, showing a first- and second-order dependence upon hydroxide ion concentration, as well as a pH-independent pathway. The pH dependence is interpreted in terms of the formation of tetrahedral intermediates in different protonic states which may break down to products via hydroxide ion, hydronium ion and water catalysed pathways. These gamma-lactams are as reactive, or more reactive, than benzylpenicillin.

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页码：23 / 28

页数：6

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