1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles
Publication type: Journal Article
Publication date: 2021-01-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
The three-component reaction of (E)-1,5-diarylpent-4-ene-1,3-diones, isatins, and (thia)proline in i-PrOH at room temperature proceeds regio- and stereoselectively leading to the formation of spiro[(thia)pyrrolizidine-3,3'-oxindoles] with the 1,3-dicarbonyl moiety in the (thia)pyrrolizidine ring. Subsequent treatment of these tetracyclic products with arylhydrazine hydrochlorides under reflux in the EtOH–AcOH system gave 5-substituted 1,3-diaryl-1H-pyrazoles in high yields.
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Korotaev V. Yu. et al. 1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 1. pp. 81-91.
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Korotaev V. Yu., Zimnitskiy N. S., Denikaev A. D., Barkov A. Yu., Kutyashev I. B., Sosnovskikh V. Ya. 1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles // Chemistry of Heterocyclic Compounds. 2021. Vol. 57. No. 1. pp. 81-91.
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TY - JOUR
DO - 10.1007/s10593-021-02871-0
UR - https://doi.org/10.1007/s10593-021-02871-0
TI - 1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles
T2 - Chemistry of Heterocyclic Compounds
AU - Korotaev, Vladislav Yu
AU - Zimnitskiy, Nikolay S
AU - Denikaev, Andrey D
AU - Barkov, Alexey Yu
AU - Kutyashev, Igor B
AU - Sosnovskikh, Vyacheslav Ya
PY - 2021
DA - 2021/01/01
PB - Springer Nature
SP - 81-91
IS - 1
VL - 57
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2021_Korotaev,
author = {Vladislav Yu Korotaev and Nikolay S Zimnitskiy and Andrey D Denikaev and Alexey Yu Barkov and Igor B Kutyashev and Vyacheslav Ya Sosnovskikh},
title = {1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles},
journal = {Chemistry of Heterocyclic Compounds},
year = {2021},
volume = {57},
publisher = {Springer Nature},
month = {jan},
url = {https://doi.org/10.1007/s10593-021-02871-0},
number = {1},
pages = {81--91},
doi = {10.1007/s10593-021-02871-0}
}
Cite this
MLA
Copy
Korotaev, Vladislav Yu., et al. “1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles.” Chemistry of Heterocyclic Compounds, vol. 57, no. 1, Jan. 2021, pp. 81-91. https://doi.org/10.1007/s10593-021-02871-0.