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1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines : experimental and theoretical study. / Vorob′ev, Aleksey Yu; Borodkin, Gennady I.; Andreev, Rodion V. et al.

In: Chemistry of Heterocyclic Compounds, Vol. 57, No. 3, 03.2021, p. 284-291.

Research output: Contribution to journal › Article › peer-review

Harvard

Vorob′ev, AY, Borodkin, GI, Andreev, RV & Shubin, VG 2021, '1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study', Chemistry of Heterocyclic Compounds, vol. 57, no. 3, pp. 284-291. https://doi.org/10.1007/s10593-021-02905-7

APA

Vorob′ev, A. Y., Borodkin, G. I., Andreev, R. V., & Shubin, V. G. (2021). 1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study. Chemistry of Heterocyclic Compounds, 57(3), 284-291. https://doi.org/10.1007/s10593-021-02905-7

Vancouver

Vorob′ev AY, Borodkin GI, Andreev RV, Shubin VG. 1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study. Chemistry of Heterocyclic Compounds. 2021 Mar;57(3):284-291. doi: 10.1007/s10593-021-02905-7

Author

Vorob′ev, Aleksey Yu ; Borodkin, Gennady I. ; Andreev, Rodion V. et al. / 1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines : experimental and theoretical study. In: Chemistry of Heterocyclic Compounds. 2021 ; Vol. 57, No. 3. pp. 284-291.

BibTeX

@article{86a025c9c2e84221bb8fab3386e6bcf6,
title = "1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines: experimental and theoretical study",
abstract = "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.",
keywords = "1,3-dipolar cycloaddition, DFT, N-imines, [1,2,4]triazolo[1,5-a]azines",
author = "Vorob′ev, {Aleksey Yu} and Borodkin, {Gennady I.} and Andreev, {Rodion V.} and Shubin, {Vyacheslav G.}",
note = "Publisher Copyright: {\textcopyright} 2021, Springer Science+Business Media, LLC, part of Springer Nature. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",
year = "2021",
month = mar,
doi = "10.1007/s10593-021-02905-7",
language = "English",
volume = "57",
pages = "284--291",
journal = "Chemistry of Heterocyclic Compounds",
issn = "0009-3122",
publisher = "Springer New York",
number = "3",

}

RIS

TY - JOUR

T1 - 1,3-Dipolar cycloaddition of cyanopyridines to heterocyclic N-imines

T2 - experimental and theoretical study

AU - Vorob′ev, Aleksey Yu

AU - Borodkin, Gennady I.

AU - Andreev, Rodion V.

AU - Shubin, Vyacheslav G.

N1 - Publisher Copyright: © 2021, Springer Science+Business Media, LLC, part of Springer Nature. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/3

Y1 - 2021/3

N2 - 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.

AB - 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.

KW - 1,3-dipolar cycloaddition

KW - DFT

KW - N-imines

KW - [1,2,4]triazolo[1,5-a]azines

UR - http://www.scopus.com/inward/record.url?scp=85103371946&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/9d00d53a-c2ff-38b7-8434-877b44928367/

U2 - 10.1007/s10593-021-02905-7

DO - 10.1007/s10593-021-02905-7

M3 - Article

AN - SCOPUS:85103371946

VL - 57

SP - 284

EP - 291

JO - Chemistry of Heterocyclic Compounds

JF - Chemistry of Heterocyclic Compounds

SN - 0009-3122

IS - 3

ER -

ID: 28256560