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

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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. / Filatov, Alexander S.; Knyazev, Nickolay A.; Molchanov, Alexander P.; Panikorovsky, Taras L.; Kostikov, Rafael R.; Larina, Anna G.; Boitsov, Vitali M.; Stepakov, Alexander V.

In: Journal of Organic Chemistry, Vol. 82, No. 2, 20.01.2017, p. 959-975.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{a98a0e5e4a9b4f90a6626364cb1ffbec,

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",

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, a-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 Nsubstituted and N-unsubstituted a-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.",

author = "Filatov, {Alexander S.} and Knyazev, {Nickolay A.} and Molchanov, {Alexander P.} and Panikorovsky, {Taras L.} and Kostikov, {Rafael R.} and Larina, {Anna G.} and Boitsov, {Vitali M.} and Stepakov, {Alexander V.}",

note = "Funding Information: We gratefully acknowledge the financial support from the Russian Science Foundation (Project No 14-13-00126). This research made use of resources from the X-ray Diffraction Centre, Centre for Magnetic Resonance, Educational Resourse Center of Chemistry, and the Centre for Chemical Analysis and Materials of Saint-Petersburg State University. Publisher Copyright: {\textcopyright} 2016 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2017",

month = jan,

day = "20",

doi = "10.1021/acs.joc.6b02505",

language = "English",

volume = "82",

pages = "959--975",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "2",

}

RIS

TY - JOUR

T1 - 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

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 M.

AU - Stepakov, Alexander V.

N1 - Funding Information: We gratefully acknowledge the financial support from the Russian Science Foundation (Project No 14-13-00126). This research made use of resources from the X-ray Diffraction Centre, Centre for Magnetic Resonance, Educational Resourse Center of Chemistry, and the Centre for Chemical Analysis and Materials of Saint-Petersburg State University. Publisher Copyright: © 2016 American Chemical Society. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2017/1/20

Y1 - 2017/1/20

N2 - 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, a-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 Nsubstituted and N-unsubstituted a-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.

AB - 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, a-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 Nsubstituted and N-unsubstituted a-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.

UR - http://www.scopus.com/inward/record.url?scp=85039770138&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.6b02505

DO - 10.1021/acs.joc.6b02505

M3 - Article

C2 - 28004934

AN - SCOPUS:85039770138

VL - 82

SP - 959

EP - 975

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -

ID: 9283827