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Synthesis and transformations of stereoisomeric ethyl 2‐isothiocyanato‐1‐cyclopentanecarboxylatesm
Author(s) -
Palkó Márta,
Fülöp Ferenc,
Evanics Ferenc,
Bernáth Gábor
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370419
Subject(s) - chemistry , alicyclic compound , thiourea , ring (chemistry) , closure (psychology) , medicinal chemistry , ethyl ester , stereochemistry , organic chemistry , market economy , economics
Ethyl vis ‐ 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.