A convenient synthesis of new 5,11-dihydroindolo{[}3,2-b]carbazoles bearing thiophene, 2,2 `-bithiophene or 2,2 `:5 `,2 `'-terthiophene units at C-2 and C-8 positions / Irgashev Roman A.,Kazin Nikita A.,Rusinov Gennady L.,Charushin Valery N. // TETRAHEDRON LETTERS. - 2017. - V. 58, l. 32. - P. 3139-3142.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

A series of new 5,11-dihydroindolo{[}3,2-b]carbazole derivatives, containing functional thiophene, 2,2'-bithiophene or 2,2':5',2 `'-terthiophene moieties at both C-2 and C-8 positions of their fused scaffolds, have been obtained from 2,8-diacetyl-substituted 5,11-dihydroindolo{[}3,2-b]carbazole compounds through the effective strategy, which is based on the sequence of two reactions, namely the Vilsmeier-Haack formylation and the Fiesselmann thiophene synthesis. The starting acetyl substituted materials have been transformed into the corresponding 3-chlorocrylaldehyde-containing compounds by treatment with POCl3-DMF complex, followed by the reaction with alkyl thioglycolates or alpha-mercaptoacetone in the presence of triethylamine to afford 2-carboalkoxythiophene- or 2-acetylthiophene-linked derivatives. 2-Acetylthiophene derivatives have further been involved into the same sequence of reactions to obtain 2,2'-bithiophene-, and 2,2':5',2 `'-terthiophene-linked 5,11-dihydroindolo{[}3,2-b]carbazole compounds. (C) 2017 Elsevier Ltd. All rights reserved.

Author keywords:

5,11-Dihydroindolo{[}3,2-b]carbazole; Thiophene; 3-Chloroacrylaldehyde; The Vilsmeier-Haack formylation; The Fiesselmann reaction HOLE-TRANSPORTING MATERIALS; LIGHT-EMITTING-DIODES; ELECTROLUMINESCENT PROPERTIES; ELECTROCHEMICAL PROPERTIES; OPTICAL-PROPERTIES; DERIVATIVES; PHOTOLUMINESCENT; TRANSISTORS; MOBILITY

DOI:

10.1016/j.tetlet.2017.06.085

Web of Science ID:

ISI:000406989100011

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 9
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	HOLE-TRANSPORTING MATERIALS; LIGHT-EMITTING-DIODES; ELECTROLUMINESCENT PROPERTIES; ELECTROCHEMICAL PROPERTIES; OPTICAL-PROPERTIES; DERIVATIVES; PHOTOLUMINESCENT; TRANSISTORS; MOBILITY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	irgashev@ios.uran.ru
Funding-Acknowledgement	Russian Science Foundation {[}16-13-10435]
Funding-Text	This research study was supported financially by the Russian Science Foundation (Project No. 16-13-10435).
Number-of-Cited-References	31
Usage-Count-Last-180-days	8
Usage-Count-Since-2013	8
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	FC6ZB