A one-pot approach to 10-(1H-1,2,3-triazol-11-yl)pyrimido{[}1,2-a]indoles via aryne-mediated transformations of 3-(pyrimidin-2-yl)-1,2,4-triazines / Kopchuk Dmitry S.,Chepchugov Nikolay V.,Khasanov Albert F.,Kovalev Igor S.,Santra Sougata,Nosova Emiliya V.,Zyryanov Grigory V.,Majee Adinath,Rusinov Vladimir L.,Chupakhin Oleg N. // TETRAHEDRON LETTERS. - 2016. - V. 57, l. 34. - P. 3862-3865.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

An efficient synthetic approach toward 10-(1H-1,2,3-triazol-1-yl)pyrimido{[}1,2-a]indoles, including fluorinated derivatives, has been developed. The transformation of the 1,2,4-triazine ring of readily available 3-(pyrimidin-2-yl)-1,2,4-triazines proceeds via reaction with in situ generated aryne intermediates. Improved methods have been developed for the synthesis of the starting 5,6-diaryl- and 6-aryl-3-(pyrimidin-2-yl)-1,2,4-triazines. The influence that the nature of the aryne intermediate has on the reaction pathway was studied. The structure of the obtained pyrimido{[}1,2-a]indoles was confirmed by single crystal X-ray crystallography. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

1,2,4-Triazines; 1,2-Dehydrobenzene; 4,5-Difluoro-1,2-dehydrobenzene; Transformations; 10-(1H-1,2,3-Triazol-1-yl)pyrimido{[}1,2-a]indoles INDOLE; 1-METHOXY-6-NITROINDOLE-3-CARBALDEHYDE; DERIVATIVES; AGENTS

DOI:

10.1016/j.tetlet.2016.07.052

Web of Science ID:

ISI:000381593400015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 24
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	INDOLE; 1-METHOXY-6-NITROINDOLE-3-CARBALDEHYDE; DERIVATIVES; AGENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	gyzyryanov@gmail.com
Funding-Acknowledgement	Russian Science Foundation {[}15-13-10033]; Council for grants of the President of the Russian Federation {[}MK-3079.2015.3]; BRNS-DAE {[}37(2)/14/35/2014-BRNS/563]
Funding-Text	This work was supported by the Russian Science Foundation (Grant \# 15-13-10033), the Council for grants of the President of the Russian Federation (grant no. MK-3079.2015.3), for A. Majee by BRNS-DAE (Ref. No. 37(2)/14/35/2014-BRNS/563, June 10, 2014).
Number-of-Cited-References	32
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	13
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	DT6KP