volume 82 issue 2 pages 959-975

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
Publication typeJournal Article
Publication date2017-01-03
scimago Q2
wos Q1
SJR0.737
CiteScore6.1
Impact factor3.6
ISSN00223263, 15206904
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.
Found 
Found 

Top-30

Journals

1
2
3
4
5
6
7
8
Organic and Biomolecular Chemistry
8 publications, 9.3%
Journal of Organic Chemistry
7 publications, 8.14%
International Journal of Molecular Sciences
7 publications, 8.14%
Asian Journal of Organic Chemistry
4 publications, 4.65%
Organic Letters
4 publications, 4.65%
Organic Chemistry Frontiers
4 publications, 4.65%
Tetrahedron
3 publications, 3.49%
ChemistrySelect
3 publications, 3.49%
New Journal of Chemistry
3 publications, 3.49%
Synthesis
3 publications, 3.49%
Russian Journal of Organic Chemistry
2 publications, 2.33%
Russian Chemical Bulletin
2 publications, 2.33%
Molecular Diversity
2 publications, 2.33%
Chemistry of Heterocyclic Compounds
2 publications, 2.33%
Tetrahedron Letters
2 publications, 2.33%
Molecules
2 publications, 2.33%
Chemical Communications
2 publications, 2.33%
RSC Advances
2 publications, 2.33%
Russian Journal of General Chemistry
2 publications, 2.33%
Chemistry - A European Journal
2 publications, 2.33%
Journal of Molecular Structure
2 publications, 2.33%
Beilstein Journal of Organic Chemistry
1 publication, 1.16%
Applied Magnetic Resonance
1 publication, 1.16%
Journal of Heterocyclic Chemistry
1 publication, 1.16%
Advanced Synthesis and Catalysis
1 publication, 1.16%
Chemistry - An Asian Journal
1 publication, 1.16%
European Journal of Organic Chemistry
1 publication, 1.16%
Chinese Journal of Chemistry
1 publication, 1.16%
Chemical Society Reviews
1 publication, 1.16%
Chemical Science
1 publication, 1.16%
1
2
3
4
5
6
7
8

Publishers

5
10
15
20
25
Royal Society of Chemistry (RSC)
21 publications, 24.42%
Wiley
15 publications, 17.44%
American Chemical Society (ACS)
11 publications, 12.79%
MDPI
10 publications, 11.63%
Springer Nature
8 publications, 9.3%
Elsevier
7 publications, 8.14%
Pleiades Publishing
4 publications, 4.65%
Georg Thieme Verlag KG
4 publications, 4.65%
Taylor & Francis
2 publications, 2.33%
Beilstein-Institut
1 publication, 1.16%
Asian Journal of Chemistry
1 publication, 1.16%
Bentham Science Publishers Ltd.
1 publication, 1.16%
The Russian Academy of Sciences
1 publication, 1.16%
5
10
15
20
25
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
87
Share
Cite this
GOST |
Cite this
GOST Copy
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) Copy
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.
RIS |
Cite this
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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.