Convenient synthesis of 3-unsubstituted oxindole-1-carboxamides

被引：0
|
作者：
Porcs-Makkay, Marta [1 ]
Volk, Balazs [1 ]
Kokai, Eszter [2 ]
Simig, Gyula [1 ]
机构：
[1] EGIS Pharmaceut Plc, Div Chem Res, H-1475 Budapest, Hungary
[2] Budapest Univ Technol & Econ, Fac Chem Engn, H-1521 Budapest, Hungary
来源：
TETRAHEDRON | 2012年 / 68卷 / 05期
关键词：
Oxindole; Amidation; Dephenoxycarbonylation; 4-N; N-Dimethylaminopyridinum; (DMAP); salt; DERIVATIVES;
D O I：
10.1016/j.tet.2011.12.027
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The multiple reactivity of the mesomeric anion formed by N- or C(3)-deprotonation of 3-unsubstituted oxindoles hampers the selective introduction of substituents onto the nitrogen atom. A conveniently applicable reaction sequence has been elaborated for the synthesis of 3-unsubstituted oxindole-1-carboxamides starting from the easily available 1,3-bis(phenoxycarbonyl)oxindoles. Selective amidation of the N-phenoxycarbonyl moiety and subsequent removal of the C(3)-phenoxycarbonyl moiety furnished the title compounds, which are useful building blocks for further functionalization. Besides the novel methodologies, several new representatives of this valuable compound family and their intermediates are also described below. (C) 2012 Elsevier Ltd. All rights reserved.
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页码：1427 / 1435
页数：9
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