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

✍ Scribed by Márta Palkó; Ferenc Fülöp; Ferenc Evanics; Gábor Bernáth

• Book ID: 102343297
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 298 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370419

✦ Synopsis

Abstract

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.