A catalyst and additive-free three-component reaction of highly electrophilic azides with cyclic ketones and cycloaliphatic amines. Synthesis of novel N-heteroaryl amidines / Efimov Ilya,Beliaev Nikolai,Beryozkina Tetyana,Slepukhin Pavel,Bakulev Vasiliy // TETRAHEDRON LETTERS. - 2016. - V. 57, l. 18. - P. 1949-1952.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Highly electrophilic 5-azido-1-methyl-4-nitro-1H-imidazole and sulfonyl azides were demonstrated to react with alicyclic amines and cyclic ketones in the absence of any catalyst or additive to afford novel N-(4-nitroimidazol-5-yl)- or N-sulfonylamidines respectively. Based on single crystal X-ray analysis, a revision of the previously reported data of Gao and co-workers on the direction of the reaction of sulfonyl azides with endocyclic enamines was made. The reaction of 2,6-diazidopyridine with an enamine, 4-(cyclohex-1-en-l-yl)morpholine, proceeded with cyclization of the azide moiety onto the pyridine C=N bond to form an amidine bearing the tetrazolo{[}1,5-a]pyridine fragment. (C) 2016 Elsevier Ltd. All rights reserved.

Author keywords:

Azide; Amine; Amidine; Triazoline; Multicomponent reaction SULFONYL AMIDINES; CYCLOADDITION REACTIONS; KETENE N,X-ACETALS; ORGANIC AZIDES; RING EXPANSION; TRIAZOLINES; ENAMINES; 1,2,3-TRIAZOLINES

DOI:

10.1016/j.tetlet.2016.03.058

Web of Science ID:

ISI:000374622800003

Соавторы в МНС:

—

Другие поля

Поле	Значение
Month	MAY 4
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	SULFONYL AMIDINES; CYCLOADDITION REACTIONS; KETENE N,X-ACETALS; ORGANIC AZIDES; RING EXPANSION; TRIAZOLINES; ENAMINES; 1,2,3-TRIAZOLINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	v.a.bakulev@urfu.ru
ResearcherID-Numbers	Efimov, Ilya/H-8741-2016
ORCID-Numbers	Efimov, Ilya/0000-0003-1123-987X
Funding-Acknowledgement	Russian Scientific Foundation {[}15-13-10031]
Funding-Text	This project was supported by the Russian Scientific Foundation (15-13-10031).
Number-of-Cited-References	42
Usage-Count-Last-180-days	5
Usage-Count-Since-2013	32
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	DK0SP