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1,3-dipolar cycloaddition of nitrones and nitrile oxides to 5,5-dimethyl-3-methylenepyrrolidine-2-thione


Fisera, Lubor; Jaroskova, Libuse; Matejkova, Iveta; Heimgartner, Heinz (1995). 1,3-dipolar cycloaddition of nitrones and nitrile oxides to 5,5-dimethyl-3-methylenepyrrolidine-2-thione. Heterocycles, 40:271-278.

Abstract

A simple synthesis of title compound (3) and a number of different cycloadditions are described. C-Aroyl- and C,N-diphenylnitrones react regio- and stereoselectively to the C=C exocyclic double bond of 3, to give only spirocycloadduct (10). On the other hand, C-phenyl-N-methylnitrone gives a mixture of diastereomeric spirocycloadducts (10) and (11). Nitrile oxides undergo 1,3-dipolar cycloaddition both to the exocyclic C=C and C=S double bonds with subsequent cycloreversion and formation of spiro-lactams (6). The appropriate spiro-thiolactams (8) were synthesized by treatment of 6 with Lawesson's reagent.

Abstract

A simple synthesis of title compound (3) and a number of different cycloadditions are described. C-Aroyl- and C,N-diphenylnitrones react regio- and stereoselectively to the C=C exocyclic double bond of 3, to give only spirocycloadduct (10). On the other hand, C-phenyl-N-methylnitrone gives a mixture of diastereomeric spirocycloadducts (10) and (11). Nitrile oxides undergo 1,3-dipolar cycloaddition both to the exocyclic C=C and C=S double bonds with subsequent cycloreversion and formation of spiro-lactams (6). The appropriate spiro-thiolactams (8) were synthesized by treatment of 6 with Lawesson's reagent.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1995
Deposited On:04 Dec 2013 13:27
Last Modified:08 Dec 2017 00:17
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Slovak Grant Agency (grant No. 1-140-93), Swiss National Science Foundation (grant No. 70TP-031628)
Publisher DOI:https://doi.org/10.3987/COM-94-S22

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