Synthesis of 6-aryl- and 5-aroylcomanic acids from 5-aroyl-2-carbethoxy-4-pyrones via a deformylative rearrangement and ring-opening/ring-closure sequence

被引：11

作者：

Obydennov, Dmitrii L. ^{[1
]}

Roeschenthaler, Gerd-Volker ^{[2
]}

Sosnovskikh, Vyacheslav Ya. ^{[1
]}

机构：

[1] Ural Fed Univ, Dept Chem, Ekaterinburg 620000, Russia

[2] Jacobs Univ Bremen, Sch Sci & Engn, D-28759 Bremen, Germany

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 02期

关键词：

Claisen condensation; 2-(Aminomethylene)butane-1,3-diones; 5-Aroyl-2-carbethoxy-4-pyrones; Rearrangement; 6-Arylcomanic acids; 5-Aroylcomanic acids; REGIOSELECTIVE SYNTHESIS; AROMATIC-AMINES; HETEROCYCLES; DERIVATIVES; AGENTS;

D O I：

10.1016/j.tetlet.2013.11.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1-aryl-2-(dimethylaminomethylene)butane-1,3-diones with diethyl oxalate in the presence of sodium hydride in THF gave ethyl 5-aroy1-4-oxo-4H-pyran-2-carboxylates, from which 4-oxo-6-aryl-4H-pyran-2-carboxylic acids (6-arylcomanic acids) were obtained in high yields via acid-catalyzed deformylative rearrangement. 5-Aroy1-4-oxo-4H-pyran-2-carboxylic acids (5-aroylcomanic acids) were prepared via a ring-opening/ring-closure sequence by the reaction of 5-aroy1-2-carbethoxy-4-pyrones with piperidine and subsequent basic hydrolysis and acidification. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：472 / 474

页数：3

共 34 条

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