1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study Full article
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Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353 |
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| 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 | ||||
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Abstract:
[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.
Cite:
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 OpenAlex
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 OpenAlex
Dates:
| Published print: | Mar 1, 2021 |
| Published online: | Mar 27, 2021 |
Identifiers:
| Web of science: | WOS:000633751800001 |
| Scopus: | 2-s2.0-85103371946 |
| Elibrary: | 46766835 |
| OpenAlex: | W3149501141 |