Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles
Publication type: Journal Article
Publication date: 2018-10-01
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
The first derivatives of 3H-pyrrol-4-amines spiro-fused with fluorene or anthrone were synthesized in a Rh2(OAc)4-catalyzed reaction of 1-sulfonyl-1,2,3-triazoles with 2H-azirines. The reaction proceeds through 1,4-diazahexa-1,3,5-triene intermediates, which under the conditions employed cyclize to stable at room temperature 1,2-dihydropyrazines. At elevated temperatures, 1,2-dihydropyrazines are in ring-chain equilibrium with 1,4-diazahexa-1,3,5-trienes, which undergo irreversible 5-exo-trig cyclization, leading to spirocyclic derivatives of 3H-pyrrol-4-amine.
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Total citations:
8
Citations from 2024:
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(12.5%)
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Khaidarov A. R. et al. Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles // Chemistry of Heterocyclic Compounds. 2018. Vol. 54. No. 10. pp. 946-950.
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Khaidarov A. R., Rostovskii N. V., Starova G. L., Khlebnikov A. F., Novikov M. S. Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles // Chemistry of Heterocyclic Compounds. 2018. Vol. 54. No. 10. pp. 946-950.
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TY - JOUR
DO - 10.1007/s10593-018-2378-8
UR - https://doi.org/10.1007/s10593-018-2378-8
TI - Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles
T2 - Chemistry of Heterocyclic Compounds
AU - Khaidarov, Adel R
AU - Rostovskii, Nikolai V
AU - Starova, Galina L
AU - Khlebnikov, Alexander F
AU - Novikov, Mikhail S.
PY - 2018
DA - 2018/10/01
PB - Springer Nature
SP - 946-950
IS - 10
VL - 54
SN - 0009-3122
SN - 1573-8353
ER -
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@article{2018_Khaidarov,
author = {Adel R Khaidarov and Nikolai V Rostovskii and Galina L Starova and Alexander F Khlebnikov and Mikhail S. Novikov},
title = {Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles},
journal = {Chemistry of Heterocyclic Compounds},
year = {2018},
volume = {54},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1007/s10593-018-2378-8},
number = {10},
pages = {946--950},
doi = {10.1007/s10593-018-2378-8}
}
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MLA
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Khaidarov, Adel R., et al. “Synthesis of spirocyclic 3Н-pyrrol-4-amines from 2H-azirines and 1-sulfonyl-1,2,3-triazoles.” Chemistry of Heterocyclic Compounds, vol. 54, no. 10, Oct. 2018, pp. 946-950. https://doi.org/10.1007/s10593-018-2378-8.