Direct arylalkenylation of furazano{[}3,4-b]pyrazines via a new C-H functionalization protocol / Kazin Nikita A.,Kvashnin Yuriy A.,Irgashev Roman A.,Dehaen Wim,Rusinov Gennady L.,Charushin Valery N. // TETRAHEDRON LETTERS. - 2015. - V. 56, l. 14. - P. 1865-1869.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

6-Styryl-5-(het)arylfurazano{[}3,4-b]pyrazines have been obtained by novel C-H functionalization, which is a particular case of the nucleophilic substitution of hydrogen (S-N(H)). The process is initiated by the Michael addition of morpholine at the C=C double bond of beta-nitrostyrenes, and the subsequent addition of the generated carbanion to C-6 of 5-(het)arylfurazano{[}3,4-b]pyrazines, followed by elimination of nitrous acid and morpholine. It has been shown that in this case, only beta-nitrostyrenes bearing electron-rich substituents on the aromatic ring are involved in arylalkenylation of furazano{[}3,4-b]pyrazines. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

C-H functionalization; Furazano{[}3,4-b]pyrazines; beta-Nitrostyrenes; Nucleophilic substitution of hydrogen; Metal-free coupling reactions; Direct arylalkenylation NUCLEOPHILIC-SUBSTITUTION; HYDROGEN; DERIVATIVES; INHIBITORS; DISCOVERY; CHEMISTRY; AGENTS; SAR

DOI:

10.1016/j.tetlet.2015.02.091

Web of Science ID:

ISI:000351790700028

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR 1
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	NUCLEOPHILIC-SUBSTITUTION; HYDROGEN; DERIVATIVES; INHIBITORS; DISCOVERY; CHEMISTRY; AGENTS; SAR
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	Russian Foundation for Basic Research {[}13-03-12434-ofi\_m2, 13-03-96049-r\_ural\_a, 14-03-01017\_A, 15-03-00924\_A]; Scientific Council of the President of the Russian Federation {[}MK-3043.2014.3]
Funding-Text	This work was supported by the Russian Foundation for Basic Research (research projects No. 13-03-12434-ofi\_m2, 13-03-96049-r\_ural\_a, 14-03-01017\_A, 15-03-00924\_A) and the Scientific Council of the President of the Russian Federation (grant MK-3043.2014.3).
Number-of-Cited-References	32
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	7
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	CE4HC