New practical synthesis of tenidap

被引：22

作者：

Porcs-Makkay, M ^{[1
]}

Simig, G ^{[1
]}

机构：

[1] Egis Pharmaceut Ltd, Div Chem Res, H-1475 Budapest, Hungary

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2000年 / 4卷 / 01期

关键词：

D O I：

10.1021/op990067a

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The development of a new, practical synthesis to tenidap is described. N,O-Dialkoxy(aryloxy)carbonylation of 5-chloro-2-oxo-2,3-dihydroindole, followed by removal of the O-alkoxy-(aryloxy)carbonyl group gave 1-[alkoxy(aryloxy)carbonyl]-5-chloro-2-oxo-2,3-dihydroindoles in good yields, The latter compounds were thenoylated in the 3-position. The role of DMAP in the acylation reaction is discussed. The structures of the thenoylated products and their enolate salts were investigated both in solution and solid phases. Ammonolysis of 5-chloro-3-[1-hydroxy-1-(2-thienyl)methylene]-2-oxo-1-phenoxycarbonyl-2,3-dihydroindole afforded the corresponding 1-carbamoyl derivative (tenidap) in high yield. The corresponding 1-ethoxy- and 1-methoxycarbonyl derivatives could not be similarly transformed to tenidap; loss of the alkoxycarbonyl moiety occurred instead of carbamoylation.

引用

页码：10 / 16

页数：7

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