Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-[1,5-a]Quinolines
Vladimir T Abaev
2
,
Tetyana V Beryozkina
1
,
Kristina A Galata
1
,
Pavel A. Slepukhin
1, 3
,
Maria A Kostenko
1
,
Vera S Berseneva
1
Тип публикации: Journal Article
Дата публикации: 2016-09-01
scimago Q4
wos Q4
БС3
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Краткое описание
The reaction of 2-azidobenzaldehydes with 2-thioamides of cyanoacetic acid proceeds without a solvent and base at 80–90°C selectively by one of the possible routes to form tetrazolo[1,5-a]quinolines. The proposed mechanism of the reaction involves the Knoevenagel condensation and subsequent intramolecular [3+2] cycloaddition of the azide group at the C≡N bond of an intermediate acrylonitrile.
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Filimonov V. O. et al. Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-[1,5-a]Quinolines // Chemistry of Heterocyclic Compounds. 2016. Vol. 52. No. 9. pp. 721-726.
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Filimonov V. O., Abaev V. T., Beryozkina T. V., Galata K. A., Slepukhin P. A., Kostenko M. A., Berseneva V. S. Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-[1,5-a]Quinolines // Chemistry of Heterocyclic Compounds. 2016. Vol. 52. No. 9. pp. 721-726.
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TY - JOUR
DO - 10.1007/s10593-016-1954-z
UR - https://doi.org/10.1007/s10593-016-1954-z
TI - Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-[1,5-a]Quinolines
T2 - Chemistry of Heterocyclic Compounds
AU - Filimonov, Valeriy O
AU - Abaev, Vladimir T
AU - Beryozkina, Tetyana V
AU - Galata, Kristina A
AU - Slepukhin, Pavel A.
AU - Kostenko, Maria A
AU - Berseneva, Vera S
PY - 2016
DA - 2016/09/01
PB - Springer Nature
SP - 721-726
IS - 9
VL - 52
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2016_Filimonov,
author = {Valeriy O Filimonov and Vladimir T Abaev and Tetyana V Beryozkina and Kristina A Galata and Pavel A. Slepukhin and Maria A Kostenko and Vera S Berseneva},
title = {Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-[1,5-a]Quinolines},
journal = {Chemistry of Heterocyclic Compounds},
year = {2016},
volume = {52},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s10593-016-1954-z},
number = {9},
pages = {721--726},
doi = {10.1007/s10593-016-1954-z}
}
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Filimonov, Valeriy O., et al. “Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-[1,5-a]Quinolines.” Chemistry of Heterocyclic Compounds, vol. 52, no. 9, Sep. 2016, pp. 721-726. https://doi.org/10.1007/s10593-016-1954-z.
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