A new and convenient synthetic way to 2-substituted thieno{[}2,3-b]indoles / Irgashev Roman A.,Karmatsky Arseny A.,Rusinov Gennady L.,Charushin Valery N. // BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - 2015. - V. 11, l. . - P. 1000-1007.

ISSN/EISSN:

1860-5397 / нет данных

Type:

Article

Abstract:

A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno{[}2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the ``aldol-crotonic{''} type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene) indolin-2-ones with Lawesson's reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal-Knorr cyclization, thus affording tricyclic thieno{[}2,3-b]indoles.

Author keywords:

aldol-crotonic condensation; isatin; Lawesson's reagent; methyl ketones; Paal-Knorr reaction; thieno{[}2,3-b]indole STREPTOMYCETE STRAIN; INDOLE-DERIVATIVES; SOLAR-CELLS; THIENODOLIN; HETEROACENES; CARBAZOLES; PYRROLE

DOI:

10.3762/bjoc.11.112

Web of Science ID:

ISI:000356323700001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN 11
Publisher	BEILSTEIN-INSTITUT
Address	TRAKEHNER STRASSE 7-9, FRANKFURT AM MAIN, 60487, GERMANY
Language	English
Keywords-Plus	STREPTOMYCETE STRAIN; INDOLE-DERIVATIVES; SOLAR-CELLS; THIENODOLIN; HETEROACENES; CARBAZOLES; PYRROLE
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	34
Usage-Count-Last-180-days	5
Usage-Count-Since-2013	23
Journal-ISO	Beilstein J. Org. Chem.
Doc-Delivery-Number	CK6FK