Synthesis and transformations of stereoisomeric ethyl 2-isothiocyanato-1-cyclopentanecarboxylates

M. Palko, F. Evanics, G. Bernath, F. Fulop

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Abstract

Ethyl cis- and trans-2-isothiocyanato-1-cyclopentanecarboxylates 2 and 7 were prepared by the reaction of the corresponding alicyclic ethyl 2-amino-1-carboxylates and thiophosgene. The cis-Isothiocyanato compound 2 underwent ring closure with amines in one or two steps, resulting in 3-substituted-cis-2-thioxocyclopenta[d]pyrimidin-4-ones 3a-g. The trans isomer 7 failed to cyclize, but gave carboxamide 8a,b or thiourea ester derivatives 9a,b.

Original languageEnglish
Pages (from-to)779-782
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume37
Issue number4
DOIs
Publication statusPublished - Jan 1 2000

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ASJC Scopus subject areas

  • Organic Chemistry

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