Regioselective Synthesis of New 5-Ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene Bromides and Rearrangement Reaction Thereof

Rade Markovi; Marija Baranac

doi:10.1055/s-2000-6596

Synlett 2000; 2000(5): 0607-0610
DOI: 10.1055/s-2000-6596

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Regioselective Synthesis of New 5-Ethoxycarbonylmethyl-4-oxothiazolidin-2-ylidene Bromides and Rearrangement Reaction Thereof

Rade Marković^* , Marija Baranac

^*Faculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 158, 11001 Belgrade, Yugoslavia; E-mail: markovic@helix.chem.bg.ac.yu

Abstract

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(Z)-5-Substituted-2-alkylidene-4-oxothiazolidine derivatives 2a - c were regioselectively brominated to afford the new, synthetically useful vinyl bromides 3a - c. They undergo novel rearrangement reaction to provide 4-oxothiazolidine derivatives 5a-c containing two fully conjugated exocyclic double bonds. Extremely clean and efficient derivatization of 2a - c to 5a - c was also achieved by a one-pot three-step sequence under mild experimental conditions without isolation of vinyl bromides 3a - c.

push-pull alkene - 4-oxothiazolidine derivatives - regioselective bromination - rearrangement reaction

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