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

Autor:	Gennady I. Borodkin, Vyacheslav G. Shubin, R. V. Andreev, Aleksey Yu. Vorob′ev
Rok vydání:	2021
Předmět:	010405 organic chemistry Chemistry Concerted reaction Organic Chemistry 1 3-Dipolar cycloaddition Reactivity (chemistry) 010402 general chemistry 01 natural sciences Medicinal chemistry Cycloaddition 0104 chemical sciences
Zdroj:	Chemistry of Heterocyclic Compounds. 57:284-291
ISSN:	1573-8353 0009-3122
DOI:	10.1007/s10593-021-02905-7
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f8c5ca3dd8db1c02f886b89659eff1b8 https://doi.org/10.1007/s10593-021-02905-7 Zobrazit plný text záznamu Plný text ve formátu PDF