1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study

1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study Full article

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

Output data

Year: 2021, Volume: 57, Number: 3, Pages: 284-291 Pages count : 8 DOI: 10.1007/s10593-021-02905-7

Tags

1,3-dipolar cycloaddition; DFT; N-imines; [1,2,4]triazolo[1,5-a]azines

Authors

Vorob′ev A.Y. ^1,2 , Borodkin G.I. ^1,2 , Andreev R.V. ¹ , Shubin V.G. ¹

Affiliations

1	N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russian Federation
2	Novosibirsk State University, 1 Pirogov St., Novosibirsk, 630090, Russian Federation

[Figure not available: see fulltext.] Series of 2-pyridyl[1,2,4]triazolo[1,5-a]azines have been synthesized by cycloaddition of cyanopyridines with N-aminoazinium mesitylenesulfonates under basic conditions (KOH/H2O). An improved protocol for pyridyl-substituted [1,2,4]triazolo[1,5-a]pyridines synthesis based on addition of H2O2 as internal oxidant has been suggested. In the case of quinolinium and isoquinolinium salts, only dimerization of the corresponding N-imines has been observed, while pyrazinium-N-imine has not shown any reactivity toward cycloaddition. DFT studies have shown that the cycloaddition proceeds through concerted mechanism. © 2021, Springer Science+Business Media, LLC, part of Springer Nature.

Vorob′ev A.Y. , Borodkin G.I. , Andreev R.V. , Shubin V.G.
1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study
Chemistry of Heterocyclic Compounds. 2021. V.57. N3. P.284-291. DOI: 10.1007/s10593-021-02905-7 WOS Scopus РИНЦ

Published print:	Mar 1, 2021
Published online:	Mar 27, 2021

Web of science	WOS:000633751800001
Scopus	2-s2.0-85103371946
Elibrary	46766835
OpenAlex	W3149501141