The first synthesis of 4-unsubstituted 3-(trifluoroacetyl)coumarins by the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by chromene-coumarin recyclization

被引：33

作者：

Chizhov, Dmitrii L. ^{[1
]}

Sosnovskikh, Vyacheslav Ya. ^{[2
]}

Pryadeina, Marina V. ^{[1
]}

Burgart, Yanina V. ^{[1
]}

Saloutin, Victor I. ^{[1
]}

Charushin, Valery N. ^{[1
]}

机构：

[1] Russian Acad Sci, I Ya Postovsky Inst Organ Synth, Ural Branch, Ekaterinburg 620041, Russia

[2] Ural State Univ, Dept Chem, Ekaterinburg 620083, Russia

来源：

SYNLETT | 2008年 / 02期

关键词：

ethyl trifluoroacetoacetate; salicylaldehydes; Knoevenagel condensation; 3-(trifluoroacetyl)coumarins; chromene-coumarin recyclization;

D O I：

10.1055/s-2007-1000867

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of ethyl 6-substituted 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates was obtained in good yields via the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate in the presence of piperidinium acetate. The subsequent recyclization of these chromenes proceeds smoothly in refluxing chlorobenzene in the presence of p-toluenesulfonic acid affording previously unknown 3-(trifluoroacetyl)coumarins in moderate to good yields.

引用

页码：281 / 285

页数：5

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