Synthesis of 2-Aryl-1,2,3-triazoles by Oxidative Cyclization of 2-(Arylazo)ethene-1,1-diamines: A One-Pot Approach / Gavlik Kseniya D.,Lesogorova Svetlana G.,Sukhorukova Ekaterina S.,Subbotina Julia O.,Slepukhin Pavel A.,Benassi Enrico,Belskaya Nataliya P. // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2016. - V. , l. 15. - P. 2700-2710.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

A one-pot approach for the synthesis of 2-aryl-5-amino-1,2,3-triazoles is reported. This approach involves a tandem nucleophilic addition of alkylamines to hydrazonoyl cyanides and in situ oxidative cyclization of the resulting 2-(aryl-azo)ethene-1,1-diamines in the presence of copper(II) acetate and air. The described one-pot procedure is characterized by good yields, excellent selectivity, methodical simplicity, and uses readily available chemicals. This method was applied to the gram-scale synthesis of 2-aryl-1,2,3-triazoles.

Author keywords:

Synthetic methods; Oxidative cyclization; Nucleophilic addition; Nitrogen heterocycles; Hydrazones; Regioselectivity CORRELATED MOLECULAR CALCULATIONS; GAUSSIAN-BASIS SETS; OREXIN RECEPTOR ANTAGONIST; CLICK CHEMISTRY; WAVE-FUNCTIONS; DERIVATIVES; THERMOCHEMISTRY; HYDRAZONES; INHIBITORS; EXCHANGE

DOI:

10.1002/ejoc.201600256

Web of Science ID:

ISI:000377251800015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	CORRELATED MOLECULAR CALCULATIONS; GAUSSIAN-BASIS SETS; OREXIN RECEPTOR ANTAGONIST; CLICK CHEMISTRY; WAVE-FUNCTIONS; DERIVATIVES; THERMOCHEMISTRY; HYDRAZONES; INHIBITORS; EXCHANGE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	enrico.benassi@sns.it n.p.belskaya@urfu.ru
ResearcherID-Numbers	Belskaya, Nataliya/S-3953-2017
ORCID-Numbers	Belskaya, Nataliya/0000-0002-2509-7916
Funding-Acknowledgement	Government of the Russian Federation {[}02.A03.21.0006]; Italian Ministero per l'Universita e la Ricerca Scientifica e Tecnologica (MIUR) {[}RBFR13PSB6]
Funding-Text	The research was supported by the Government of the Russian Federation (Act 211, contract number 02.A03.21.0006). E. B. wishes to thank the Italian Ministero per l'Universita e la Ricerca Scientifica e Tecnologica (MIUR) for fundings (FIRB 2013, RBFR13PSB6).
Number-of-Cited-References	58
Usage-Count-Last-180-days	5
Usage-Count-Since-2013	16
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	DN7JP