A one-pot, Ugi four-component synthesis of 2(3H)-oxazolone 4-carboxamides

被引：13
作者：
Garcia-Valverde, M. [1 ]
Macho, S. [1 ]
Marcaccini, S. [2 ]
Rodriguez, T. [1 ]
Rojo, J. [1 ]
Torroba, T. [1 ]
机构：
[1] Univ Burgos, Fac Ciencias, Dept Quim, Burgos 09001, Spain
[2] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50121 Sesto Fiorentino, Italy
来源：
SYNLETT | 2008年 / 01期
关键词：
isocyanide; arylglyoxal; trichloroacetic acid; oxazolone;
D O I：
10.1055/s-2007-992372
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ugi reaction between arylglyoxals, anilines, cyclohexyl isocyanidc and trichloroacetic acid in dichloromethane, in the presence of molecular sieves, afforded 2(3H)-oxazolone 4-carboxamides in good yields by a one-pot process that involved an in situ spontaneous cyclization of the Ugi product through an intermediate ketone enolate and the chloroacetate carbonyl group. The synthesis is based on the ability of the trichloroacetyl group to function as a masked carbonic acid surrogate.
引用
收藏
页码：33 / 36
页数：4
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