Synthesis and Transformations of Stereoisomeric Ethyl 2-Isothiocyanato-1-cyclopentqanecarboxylates

摘要

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.