A new route towards dithienoquinazoline and benzo{[}f]thieno{[}3,2-h]quinazoline systems using Pd-catalyzed intramolecular cyclization under microwave irradiation / Verbitskiy Egor V.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // ARKIVOC. - 2016. - V. , l. 4. - P. 204-216.

ISSN/EISSN:

1551-7004 / 1551-7012

Type:

Article

Abstract:

A novel synthetic route to novel thienoacene systems bearing a fused pyrimidine ring is proposed. The commercially available 5-bromopyrimidine is used as the starting material to obtain various dithienoquinazoline and benzo{[}f]thieno{[}3,2-h] quinazoline systems through the Suzuki cross-coupling, nucleophilic aromatic substitution of hydrogen (the S-N(H) reaction), and finally palladium-catalyzed intramolecular cyclization under microwave irradiation. Redox properties of some of the new compounds have been investigated. The data obtained show that these systems have plausible potential for use in organic electronic applications.

Author keywords:

Pyrimidines; thienoacenes; fused ring systems; intramolecular cyclization; palladium NUCLEOPHILIC AROMATIC-SUBSTITUTION; HYDROGEN; ARYLATION; POLYARENES; S-N(H)

DOI:

10.3998/ark.5550190.p009.623

Web of Science ID:

ISI:000377613000016

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ARKAT USA INC
Address	C/O ALAN R KATRITZKY, UNIV FLORIDA, DEPT CHEMISTRY, PO BOX 117200, GAINESVILLE, FL 32611 USA
Language	English
EISSN	1551-7012
Keywords-Plus	NUCLEOPHILIC AROMATIC-SUBSTITUTION; HYDROGEN; ARYLATION; POLYARENES; S-N(H)
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	Verbitsky@ios.uran.ru
Funding-Acknowledgement	Russian Science Foundation {[}16-13-10435]; Act 211 Government of the Russian Federation {[}02.A03.21.0006]
Funding-Text	The research was financially supported by the Russian Science Foundation (Project No. 16-13-10435) and by Act 211 Government of the Russian Federation, contract No 02.A03.21.0006. We are grateful to, Dr. A.N. Kozitsina, Dr. A.V. Ivanova, Ms. T.S. Svalova for cyclic voltammograms and Dr. M.G. Pervova for GC-MS spectra.
Number-of-Cited-References	28
Usage-Count-Since-2013	6
Journal-ISO	Arkivoc
Doc-Delivery-Number	DO2MC