Unexpected formation of diethyl 2-ethoxy-6-CF3-2H-pyran-3,5-dicarboxylate from the condensation of ethyl 4,4,4-trifluoroacetoacetate with CH(OEt)(3) / Kudyakova Yulia S.,Bazhin Denis N.,Slepukhin Pavel A.,Burgart Yanina V.,Saloutin Victor I.,Charushin Valery N. // TETRAHEDRON LETTERS. - 2017. - V. 58, l. 8. - P. 744-747.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

The one-step preparation of diethyl 2-ethoxy-6-CF3-2H-pyran-3,5-dicarboxylate via the condensation of ethyl 4,4,4-trifluoroacetoacetate with CH(OEt)(3) has been reported and a plausible mechanism for this transformation is discussed. To demonstrate the synthetic potential of the obtained pyran, the reactions with ammonia and aromatic amines to give trifluoromethylated pyridine derivatives are presented. (C) 2017 Elsevier Ltd. All rights reserved.

Author keywords:

Pyran; Detrifluoroacetylation; Ethyl trifluoroacetoacetate; Condensation; Pyridines BUILDING-BLOCKS; INHIBITORS; CONVENIENT; KETONES; 3-COMPONENT; ESTERS; WATER

DOI:

10.1016/j.tetlet.2017.01.026

Web of Science ID:

ISI:000394194100009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB 22
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	BUILDING-BLOCKS; INHIBITORS; CONVENIENT; KETONES; 3-COMPONENT; ESTERS; WATER
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dnbazhin@gmail.com
ResearcherID-Numbers	Kudyakova, Yulia/J-7484-2016 Burgart, Yanina/T-8025-2017
ORCID-Numbers	Kudyakova, Yulia/0000-0003-0637-1606 Burgart, Yanina/0000-0001-6061-2410
Funding-Acknowledgement	Russian Foundation for Basic Research {[}16-33-60048 mol\_a\_dk]; Russian Federation {[}1895.2016.4]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (grant no. 16-33-60048 mol\_a\_dk). BDN is thankful for scholarship of the President of the Russian Federation (1895.2016.4).
Number-of-Cited-References	36
Usage-Count-Since-2013	3
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	EK8SH