Nucleophilic Ring Opening of Donor–Acceptor Cyclopropanes with the Cyanate Ion: Access to Spiro[pyrrolidone-3,3′-oxindoles]

The nucleophilic ring opening of donor–acceptor cyclopropanes with the cyanate ion is reported for the first time. Cyclopropanes, spiro-activated with oxindole fragments as acceptors, are shown to undergo transformations into biologically relevant spiro­[pyrrolidone-3,3′-oxindoles] while being treat...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-08, Vol.83 (15), p.8695-8709
Main Authors: Zaytsev, Sergey V, Ivanov, Konstantin L, Skvortsov, Dmitry A, Bezzubov, Stanislav I, Melnikov, Mikhail Ya, Budynina, Ekaterina M
Format: Article
Language:English
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Summary:The nucleophilic ring opening of donor–acceptor cyclopropanes with the cyanate ion is reported for the first time. Cyclopropanes, spiro-activated with oxindole fragments as acceptors, are shown to undergo transformations into biologically relevant spiro­[pyrrolidone-3,3′-oxindoles] while being treated with potassium cyanate under microwave assistance.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00922