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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• 作者：Alexander S. Filatov ; Nickolay A. Knyazev ; Alexander P. Molchanov ; Taras L. Panikorovsky ; Rafael R. Kostikov ; Anna G. Larina ; Vitali M. BoitsovAlexander V. Stepakov
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：82
• 期：2
• 页码：959-975
• 全文大小：880K
• ISSN：1520-6904

文摘

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.