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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Published inJournal of organic chemistry Vol. 83; no. 15; pp. 8695 - 8709
Main Authors Zaytsev, Sergey V, Ivanov, Konstantin L, Skvortsov, Dmitry A, Bezzubov, Stanislav I, Melnikov, Mikhail Ya, Budynina, Ekaterina M
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2018
Amer Chemical Soc
Subjects
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Lewis bases
microwave treatment
organic chemistry
organic compounds
Physical Sciences
potassium cyanate
Science & Technology
KETONES
ROUTE
LEWIS-ACID
STRATEGY
CONSTRUCTION
AZIDE
CYCLIZATION
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b00922