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 / Obydennov Dmitrii L.,Roeschenthaler Gerd-Volker,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON LETTERS. - 2014. - V. 55, l. 2. - P. 472-474.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

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.

Author keywords:

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

DOI:

10.1016/j.tetlet.2013.11.066

Web of Science ID:

ISI:000329946900044

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 8
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	6-(TRIFLUOROMETHYL)COMANIC ACID; REGIOSELECTIVE SYNTHESIS; AROMATIC-AMINES; CHELIDONIC ACID; DERIVATIVES; HETEROCYCLES; AGENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dobydennov@mail.ru
Funding-Acknowledgement	Deutsche Forschungsgemeinschaft {[}RO 362/45-1]; Ural Federal University development program
Funding-Text	This work was carried out under the terms of the Ural Federal University development program with financial support for young scientists. The authors also thank Deutsche Forschungsgemeinschaft for financial support (Grant No. RO 362/45-1).
Number-of-Cited-References	34
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	6
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	293BR