3-Cyano-2-azaanthracene-based ``push-pull{''} fluorophores: A one-step preparation from 5-cyano-1,2,4-triazines and 2,3-dehydronaphthalene, generated in situ / Kopchuk Dmitry S.,Chepchugov Nikolay V.,Taniya Olga S.,Khasanov Albert F.,Giri Kousik,Kovalev Igor S.,Santra Sougata,Zyryanov Grigory V.,Majee Adinath,Rusinov Vladimir L.,Chupakhin Oleg N. // TETRAHEDRON LETTERS. - 2016. - V. 57, l. 50. - P. 5639-5643.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

A facile one-step approach towards 3-cyano-2-azaanthracenes via the {[}4+2] cycloaddition reaction between 5-cyano-1,2,4-triazines and 2,3-dehydronaphthalene, generated in situ from commercially available 3-amino-2-naphthoic acid, has been reported. The influence of the 1,2,4-triazine ring substituents nature on the product yield has been studied. The observed experimental results were confirmed by DFT calculations of the HOMO-LUMO energy levels of the both cycloaddends. The photophysical properties of the products have been investigated. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

1,2,4-Triazine; 2,3-Dehydronaphthalene; Aza-Diels-Alder reaction; 2-Azaanthracene-based fluorophores; Photophysical properties INVERSE-ELECTRON-DEMAND; DIELS-ALDER REACTIONS; CYANO-O-TOLUNITRILE; INTERNAL ALKYNES; BOND ACTIVATION; PRIMARY AMINES; ISOQUINOLINES; COMPLEXES; PHOTODIMERIZATION; 2,2'-BIPYRIDINE

DOI:

10.1016/j.tetlet.2016.11.008

Web of Science ID:

ISI:000389293100022

Соавторы в МНС:

Другие поля

Поле	Значение
Month	DEC 14
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	INVERSE-ELECTRON-DEMAND; DIELS-ALDER REACTIONS; CYANO-O-TOLUNITRILE; INTERNAL ALKYNES; BOND ACTIVATION; PRIMARY AMINES; ISOQUINOLINES; COMPLEXES; PHOTODIMERIZATION; 2,2'-BIPYRIDINE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	gvzyryanov@gmail.com
Funding-Acknowledgement	Russian Scientific Fund {[}15-13-10033]; Council for Grants of the President of the Russian Federation {[}MK-3079.2015.3]; BRNS, India {[}37(2)/14/35/2014-BRNS/563]
Funding-Text	S. Santra, A.F. Khasanov, I. S. Kovalev and G. V. Zyryanov are pleased to acknowledge the Russian Scientific Fund (Grant \# 15-13-10033) for funding. D. S. Kopchuk is pleased to acknowledge the financial support from Council for Grants of the President of the Russian Federation (Grant \# MK-3079.2015.3). A. Majee is pleased to acknowledge the financial support from BRNS, India (Grant \# 37(2)/14/35/2014-BRNS/563).
Number-of-Cited-References	80
Usage-Count-Last-180-days	8
Usage-Count-Since-2013	15
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	EE0TZ