3 years ago

3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles]

3-(2-Azidoethyl)oxindoles: Advanced Building Blocks for One-Pot Assembly of Spiro[pyrrolidine-3,3′-oxindoles]
Ekaterina M. Budynina, Mikhail Ya Melnikov, Nataliya S. Vorobyeva, Alexander G. Majouga, Andrey A. Akaev, Elena V. Villemson
A new synthetic approach to biologically relevant spiro[pyrrolidine-3,3′-oxindoles] was developed on the basis of the cascade transformation of 3-(2-azidoethyl)oxindoles via Staudinger/aza-Wittig/Mannich reactions. The parent azides were readily synthesized through a nucleophilic ring opening of spiro[cyclopropane-1,3′-oxindoles] with the azide ion. A series of new spiro[pyrrolidine-3,3′-oxindoles] with various (het)aryl substituents at the C2 and C5 positions of the pyrrolidine ring were synthesized. In vitro experiments revealed their high cytotoxicity toward LNCaP and PC-3 tumor cell lines.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00529

DOI: 10.1021/acs.joc.7b00529

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