Synthesis and transformations of stereoisomeric ethyl 2‐isothiocyanato‐1‐cyclopentanecarboxylatesm | Zendy

Palkó Márta | Zendy; Fülöp Ferenc | Zendy; Evanics Ferenc | Zendy; Bernáth Gábor | Zendy

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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.

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