Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition
Alexander S. Filatov
1
,
Nickolay A. Knyazev
2, 3
,
Taras L Panikorovsky
1
,
Rafael R. Kostikov
1
,
Anna G Larina
1
,
Vitali Boitsov
2, 4
,
Alexander Stepakov
1, 5
Publication type: Journal Article
Publication date: 2017-01-03
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
28004934
Organic Chemistry
Abstract
3-Spiro[cyclopropa[a]pyrrolizine]- and 3-spiro[3-azabicyclo[3.1.0]hexane]oxindoles were prepared in moderate to high yields via one-pot three-component reactions using substituted isatins, α-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated azomethine ylide onto a cyclopropene. Both N-substituted and N-unsubstituted α-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the azomethine ylide generation. The anticancer activity of some of the obtained compounds against human leukemia K562 cell line was evaluated by flow cytometry in vitro.
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Total citations:
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Citations from 2024:
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GOST
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Filatov A. S. et al. Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition // Journal of Organic Chemistry. 2017. Vol. 82. No. 2. pp. 959-975.
GOST all authors (up to 50)
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Filatov A. S., Knyazev N. A., Molchanov A. P., Panikorovsky T. L., Kostikov R. R., Larina A. G., Boitsov V., Stepakov A. Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition // Journal of Organic Chemistry. 2017. Vol. 82. No. 2. pp. 959-975.
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RIS
Copy
TY - JOUR
DO - 10.1021/acs.joc.6b02505
UR - https://doi.org/10.1021/acs.joc.6b02505
TI - Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition
T2 - Journal of Organic Chemistry
AU - Filatov, Alexander S.
AU - Knyazev, Nickolay A.
AU - Molchanov, Alexander P.
AU - Panikorovsky, Taras L
AU - Kostikov, Rafael R.
AU - Larina, Anna G
AU - Boitsov, Vitali
AU - Stepakov, Alexander
PY - 2017
DA - 2017/01/03
PB - American Chemical Society (ACS)
SP - 959-975
IS - 2
VL - 82
PMID - 28004934
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
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@article{2017_Filatov,
author = {Alexander S. Filatov and Nickolay A. Knyazev and Alexander P. Molchanov and Taras L Panikorovsky and Rafael R. Kostikov and Anna G Larina and Vitali Boitsov and Alexander Stepakov},
title = {Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.joc.6b02505},
number = {2},
pages = {959--975},
doi = {10.1021/acs.joc.6b02505}
}
Cite this
MLA
Copy
Filatov, Alexander S., et al. “Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition.” Journal of Organic Chemistry, vol. 82, no. 2, Jan. 2017, pp. 959-975. https://doi.org/10.1021/acs.joc.6b02505.