Synthesis of 4-(thien-2-yl)-substituted coumarins through Lewis acid catalyzed Michael addition of thiophenes to 3-benzoylcoumarins followed by oxidation / Irgashev Roman A.,Karmatsky Arseny A.,Rusinov Gennady L.,Charushin Valery N. // TETRAHEDRON LETTERS. - 2014. - V. 55, l. 26. - P. 3603-3606.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

3-Benzoyl-4-(thien-2-yl)coumarins have been obtained in good yields according to the S-N(H), addition-oxidation protocol, involving the diastereoselective addition of thiophenes at C-4 of 3-benzoylcoumarins under BBr3 catalysis, followed by oxidation of the intermediate 3,4-trans-3-benzoyl-4-(thien-2-yl)-3, 4-dihydrocoumarins with DDQ. This two-step procedure can be regarded as nucleophilic substitution of hydrogen (S-N(H)) on the heterocyclic ring of coumarins. (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

Thiophenes; 3-Benzoylcoumarins; Lewis acid; Nucleophilic aromatic substitution of hydrogen; Metal-free cross-coupling reactions; Direct heteroarylation SENSITIZED SOLAR-CELLS; BIOLOGICAL EVALUATION; DERIVATIVES; HYDROGEN; SUBSTITUTION; DYES

DOI:

10.1016/j.tetlet.2014.04.112

Web of Science ID:

ISI:000337868300007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN 25
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	SENSITIZED SOLAR-CELLS; BIOLOGICAL EVALUATION; DERIVATIVES; HYDROGEN; SUBSTITUTION; DYES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	irgashev@ios.uran.ru
ResearcherID-Numbers	Irgashev, Roman/E-5077-2017
ORCID-Numbers	Irgashev, Roman/0000-0002-8428-1748
Funding-Acknowledgement	Ural Division of the Russian Academy of Sciences {[}12-P-3-1014, 12-P-3-1030, 12-T-3-1025, 12-T-3-1031]; Russian Foundation for Basic Research {[}13-03-12434-ofi\_m2, 13-0396049-r\_ural\_a, 14-03-01017\_A, 14-03-00479\_A]; Scientific Council of the President of the Russian Federation {[}MK-3043.2014.3]
Funding-Text	This work was supported by the Ural Division of the Russian Academy of Sciences (Grants nos. 12-P-3-1014, 12-P-3-1030, 12-T-3-1025 and 12-T-3-1031), the Russian Foundation for Basic Research (research projects nos. 13-03-12434-ofi\_m2, 13-0396049-r\_ural\_a, 14-03-01017\_A, 14-03-00479\_A), and the Scientific Council of the President of the Russian Federation (grant MK-3043.2014.3).
Number-of-Cited-References	26
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	24
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	AJ7HR