Regioselective C2-and C8-Acylation of 5,11-Dihydroindolo{[}3,2-b]carbazoles and the Synthesis of Their 2,8-Bis(quinoxalinyl) Derivatives / Irgashev Roman A.,Kazin Nikita A.,Kim Grigory A.,Rusinov Gennady L.,Charushin Valery N. // SYNTHESIS-STUTTGART. - 2015. - V. 47, l. 22. - P. 3561-3572.

ISSN/EISSN:

0039-7881 / 1437-210X

Type:

Article

Abstract:

An efficient approach for the double acetylation of 5,11-dihexyl- 6,12-di(hetero) aryl-substituted 5,11-dihydroindolo{[}3,2-b] carbazoles with acetic anhydride in the presence of boron trifluoride etherate has been developed, thus affording the corresponding 2,8-diacetyl derivatives in good yields. A similar acylation has been shown to occur by the reaction of anhydrides of other carboxylic acids. Oxidation of the obtained 2,8-diacetyl derivatives with selenium dioxide takes place on heating or under microwave irradiation, thus resulting in the formation of the corresponding 2,8-diglyoxals. The latter proved to react with aromatic o-diamines to afford new indolo{[}3,2-b] carbazoles bearing quinoxalinyl fragments at C-2 and C-8. Major optical properties of quinoxaline- containing indolo{[}3,2-b] carbazoles have been measured.

Author keywords:

5,11-dihydroindolo{[}3,2-b]carbazoles; acylation; 2-arylgly-oxals; quinoxalines; ladder-type heteroacenes BLUE FLUORESCENT EMITTERS; FIELD-EFFECT TRANSISTORS; LIGHT-EMITTING-DIODES; AH RECEPTOR; ACENES; MICRORIBBONS; PRECURSORS; ALDEHYDES; DESIGN; SINGLE

DOI:

10.1055/s-0035-1560183

Web of Science ID:

ISI:000365304600014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV
Publisher	GEORG THIEME VERLAG KG
Address	RUDIGERSTR 14, D-70469 STUTTGART, GERMANY
Language	English
EISSN	1437-210X
Keywords-Plus	BLUE FLUORESCENT EMITTERS; FIELD-EFFECT TRANSISTORS; LIGHT-EMITTING-DIODES; AH RECEPTOR; ACENES; MICRORIBBONS; PRECURSORS; ALDEHYDES; DESIGN; SINGLE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	irgashev@ios.uran.ru
ResearcherID-Numbers	Irgashev, Roman/E-5077-2017 Kim, Grigory/P-3806-2017
ORCID-Numbers	Irgashev, Roman/0000-0002-8428-1748 Kim, Grigory/0000-0001-8814-5180
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	45
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	7
Journal-ISO	Synthesis
Doc-Delivery-Number	CW9FR