One-Pot Domino Synthesis of Polyfunctionalized Benzophenones, Dihydroxanthones, and m-Terphenyls from 2-(Polyfluoroalkyl)chromones / Sosnovskikh Vyacheslav Ya,Korotaev Vladislav Yu,Barkov Alexey Yu,Kutyashev Igor B.,Safrygin Alexander V. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2015. - V. , l. 9. - P. 1932-1944.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

Whereas 2-(polyfluoroalkyl)chromones activated by electron-withdrawing substituents in the benzene ring react with 2-(1-phenylalkylidene)malononitriles in the presence of triethylamine in dichloromethane to produce a wide range of polyfunctionalized benzophenones and dihydroxanthones, their reactions with ethyl -cyano--methylcinnamate under the same conditions took an entirely different course and gave mainly m-terphenyl derivatives. The difference in behavior between the ylidene derivatives of malononitrile and those of ethyl cyanoacetate is remarkable.

Author keywords:

Domino reactions; Molecular diversity; Fluorine; Arenes VINYLOGOUS ALDOL REACTION; SUBSTITUTED ANILINES; MICHAEL ADDITION; AQUEOUS-MEDIA; DERIVATIVES; 2-POLYFLUOROALKYLCHROMONES; INHIBITORS; MALONONITRILES; REARRANGEMENT; OPTIMIZATION

DOI:

10.1002/ejoc.201403585

Web of Science ID:

ISI:000351207100010

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	VINYLOGOUS ALDOL REACTION; SUBSTITUTED ANILINES; MICHAEL ADDITION; AQUEOUS-MEDIA; DERIVATIVES; 2-POLYFLUOROALKYLCHROMONES; INHIBITORS; MALONONITRILES; REARRANGEMENT; OPTIMIZATION
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
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]; Ural Federal University through the Young scientists UrFU program
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (grant number 14-03-00179) and by Ural Federal University through the Young scientists UrFU program and performed within the State Task from the Ministry of Education and Science of Russian Federation.
Number-of-Cited-References	56
Usage-Count-Since-2013	19
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	CD6NX