Direct (het)arylation of {[}1,2,4]triazolo{[}1,5-a]pyrimidines: Both eliminative and oxidative pathways / Rasputin Nikolay A.,Demina Nadezhda S.,Irgashev Roman A.,Rusinov Gennady L.,Chupakhin Oleg N.,Charushin Valery N. // TETRAHEDRON. - 2017. - V. 73, l. 37. - P. 5500-5508.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

(Hetero)arylation of {[}1,2,4]triazolo{[}1,5-a]pyrimidine through the direct nucleophilic C-H functionalization of the C-7 and C-5 positions has been implemented. The regioselective addition of a (het)aryl magnesium bromide to C-7 of 6-bromo-{[}1,2,4]triazolo{[}1,5-alpyrimidine, followed by eliminative aromatization of the intermediate sigma(H)-adducts, has afforded 7-(hetero)aryl-substituted {[}1,2,4]triazolo{[}1,5-a]pyrimidines (the S-N(H) reaction, proceeding according to the ``addition-elimination{''} scheme). A second treatment with a Grignard reagent has resulted in the C-5 sigma(H)-adducts, which have been oxidized while being N-magnesium salts into 11,2,41]triazolo{[}1,5-a]pyrimidines, bearing various combinations of (hetero) aromatic substituents at C-5 and C-7 (the S-N(H) process, realizing via the ``addition-oxidation{''} scheme). As a result of optical and electrochemical studies, the obtained compounds have proved to be promising luminescent dyes and push-pull systems. (C) 2017 Elsevier Ltd. All rights reserved.

Author keywords:

{[}1,2,4]Triazolo{[}1,5-a]pyrimidine; (Het)aryl magnesium bromide; Direct (het)arylation; Nucleophilic aromatic substitution of hydrogen (S-N(H)) VINYLOGOUS IMINIUM SALTS; NUCLEOPHILIC-SUBSTITUTION; PYRIMIDINE-DERIVATIVES; BIOLOGICAL EVALUATION; INHIBITORS; HYDROGEN; AGENTS; TRIAZOLOPYRIMIDINES; HETEROCYCLIZATION; SYSTEMS

DOI:

10.1016/j.tet.2017.07.042

Web of Science ID:

ISI:000410870500004

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP 14
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	VINYLOGOUS IMINIUM SALTS; NUCLEOPHILIC-SUBSTITUTION; PYRIMIDINE-DERIVATIVES; BIOLOGICAL EVALUATION; INHIBITORS; HYDROGEN; AGENTS; TRIAZOLOPYRIMIDINES; HETEROCYCLIZATION; SYSTEMS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	nar@ios.uran.ru
Funding-Acknowledgement	Russian Science Foundation {[}16-13-10435]
Funding-Text	This work was supported by the Russian Science Foundation (Project No. 16-13-10435).
Number-of-Cited-References	42
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	2
Journal-ISO	Tetrahedron
Doc-Delivery-Number	FH0ZZ