jo6b02505_si_004.cif (26.07 kB)
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
dataset
posted on 2016-12-22, 00:00 authored by Alexander
S. Filatov, Nickolay A. Knyazev, Alexander P. Molchanov, Taras L. Panikorovsky, Rafael R. Kostikov, Anna G. Larina, Vitali M. Boitsov, Alexander V. Stepakov3-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.