Nitration of 5,11-dihydroindolo{[}3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives / Irgashev Roman A.,Kazin Nikita A.,Rusinov Gennady L.,Charushin Valery N. // BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - 2017. - V. 13, l. . - P. 1396-1406.

ISSN/EISSN:

1860-5397 / нет данных

Type:

Article

Abstract:

A new general approach to double nitration of 6,12-di(hetero)aryl-substituted and 6,12-unsubstituted 5,11-dialkyl-5,11-dihydroindolo{[}3,2-b]carbazoles by acetyl nitrate has been developed to obtain their 2,8-dinitro and 6,12-dinitro derivatives, respectively. A formation of mono-nitro derivatives (at C-2 or C-6) from the same indolo{[}3,2-b]carbazoles has also been observed in several cases. Reduction of 2-nitro and 2,8-dinitro derivatives with zinc powder and hydrochloric acid has afforded 2-amino- and 2,8-diamino-substituted indolo{[}3,2-b]carbazoles, while reduction of 6,12-dinitro derivatives under similar reaction conditions has been accompanied by denitrohydrogenation of the latter compounds into 6,12-unsubstituted indolo{[}3,2-b]carbazoles. Formylation of 6,12-dinitro derivatives has proved to occur only at C-2, while bromination of these compounds has taken place at both C-2 and C-8 of indolo{[}3,2-b]carbazole scaffold. Moreover, 6,12-dinitro-substituted indolo{[}3,2-b]carbazoles have been modified by the reactions with S- and N-nucleophiles. Notably, the treatment of 6,12-dinitro compounds with potassium thiolates has resulted in the displacement of both nitro groups, unlike potassium salts of indole or carbazole, which have caused substitution of only one nitro group.

Author keywords:

electrophilic aromatic substitution; indolo{[}3,2-b] carbazole; N-heteroacenes; nitration; nucleophilic aromatic substitution PEROVSKITE SOLAR-CELLS; LIGHT-EMITTING-DIODES; ELECTROLUMINESCENT PROPERTIES; NITRO DISPLACEMENT; AHR ACTIVATION; PHOTOLUMINESCENT; ELECTRONICS; CARBAZOLES; MOIETIES; TCDD

DOI:

10.3762/bjoc.13.136

Web of Science ID:

ISI:000405435000001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL 14
Publisher	BEILSTEIN-INSTITUT
Address	TRAKEHNER STRASSE 7-9, FRANKFURT AM MAIN, 60487, GERMANY
Language	English
Keywords-Plus	PEROVSKITE SOLAR-CELLS; LIGHT-EMITTING-DIODES; ELECTROLUMINESCENT PROPERTIES; NITRO DISPLACEMENT; AHR ACTIVATION; PHOTOLUMINESCENT; ELECTRONICS; CARBAZOLES; MOIETIES; TCDD
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	irgashev@ios.uran.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}15-03-00924\_A, 16-33-00157-mol\_a]; Scientific Council of the President of the Russian Federation {[}MK-4509.2016.3]
Funding-Text	This work was supported by the Russian Foundation for Basic Research (research projects No. 15-03-00924\_A, 16-33-00157-mol\_a), and the Scientific Council of the President of the Russian Federation (grant MK-4509.2016.3).
Number-of-Cited-References	54
Usage-Count-Last-180-days	12
Usage-Count-Since-2013	12
Journal-ISO	Beilstein J. Org. Chem.
Doc-Delivery-Number	FA4TB