One-pot synthesis of functionalized benzo{[}c]-coumarins and their precursors via the reaction of 2-(polyfluoroalkyl)chromones with 4-alkyl-3-cyanocoumarins / Sosnovskikh Vyacheslav Ya.,Korotaev Vladislav Yu.,Kutyashev Igor B.,Barkov Alexey Yu.,Safrygin Alexander V. // RSC ADVANCES. - 2016. - V. 6, l. 63. - P. 58188-58202.

ISSN/EISSN:

2046-2069 / нет данных

Type:

Article

Abstract:

2-(Polyfluoroalkyl) chromones react with 4-alkyl-3-cyanocoumarins in dichloromethane in the presence of triethylamine to give a wide variety of functionalized benzo{[}c] coumarin derivatives in good yields. This new annulation reaction presumably proceeds by a tandem intermolecular Michael addition and subsequent intramolecular condensation between an intermediate enolate anion and cyano group. In the case of 3-cyano-4-methylcoumarin and 2-(trifluoromethyl) chromones activated by two electron-withdrawing substituents, three acyclic intermediates were isolated and the possible mechanism of the reaction was suggested.

Author keywords:

1,3-BIS(SILYL ENOL ETHERS); REGIOSELECTIVE SYNTHESIS; HETEROCYCLIC SYNTHESIS; MEDICINAL CHEMISTRY; PRIVILEGED SCAFFOLD; EFFICIENT SYNTHESIS; DOMINO REACTIONS; DERIVATIVES; 2-POLYFLUOROALKYLCHROMONES; COUMARINS

DOI:

10.1039/c6ra12492e

Web of Science ID:

ISI:000378725800049

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Keywords-Plus	1,3-BIS(SILYL ENOL ETHERS); REGIOSELECTIVE SYNTHESIS; HETEROCYCLIC SYNTHESIS; MEDICINAL CHEMISTRY; PRIVILEGED SCAFFOLD; EFFICIENT SYNTHESIS; DOMINO REACTIONS; DERIVATIVES; 2-POLYFLUOROALKYLCHROMONES; COUMARINS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-00179]; Act 211 Government of the Russian Federation {[}02.A03.21.0006]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grant No. 14-03-00179), the Act 211 Government of the Russian Federation (agreement No. 02.A03.21.0006), and performed within the State Task from the Ministry of Education and Science of Russian Federation.
Number-of-Cited-References	53
Usage-Count-Since-2013	2
Journal-ISO	RSC Adv.
Doc-Delivery-Number	DP8CP