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.

Autor: Filatov AS; Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation., Knyazev NA; Saint-Petersburg Academic University - Nanotechnology Research and Education Centre RAS , ul. Khlopina 8/3, St. Petersburg, 194021, Russian Federation.; Institute of Cytology of the Russian Academy of Science , Tikhoretsky pr. 4, St. Petersburg 194064, Russian Federation., Molchanov AP; Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation., Panikorovsky TL; Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation., Kostikov RR; Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation., Larina AG; Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation., Boitsov VM; Saint-Petersburg Academic University - Nanotechnology Research and Education Centre RAS , ul. Khlopina 8/3, St. Petersburg, 194021, Russian Federation.; Pavlov First Saint Petersburg State Medical University , ul. L'va Tolstogo 6/8, St. Petersburg 197022, Russian Federation., Stepakov AV; Saint-Petersburg State University , 7/9 Universitetskaya nab., St. Petersburg, 199034, Russian Federation.; Voeikov Main Geophysical Observatory , ul. Karbysheva 7, St. Petersburg 194021, Russian Federation.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2017 Jan 20; Vol. 82 (2), pp. 959-975. Date of Electronic Publication: 2017 Jan 03.
DOI: 10.1021/acs.joc.6b02505
Abstrakt: 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.
Databáze: MEDLINE
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