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Diastereoselective Synthesis of Functionalized Tetrahydropyrimidin‐2‐thiones via ZnCl 2 Promoted One‐pot Reactions
Author(s) -
Liu Zhenming,
Zhang Lili,
Sun Jing,
Yan Chaoguo
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300577
Subject(s) - chemistry , morpholine , pyrrolidine , piperidine , thiourea , organic chemistry , zinc , medicinal chemistry , aromatization , ethanol , catalysis
In the presence of zinc chloride, the in situ generated β‐ enamino ester from the reaction of morpholine, piperidine and pyrrolidine with methyl propiolate reacted, with aromatic aldehydes and thiourea in ethanol resulting in the functionalized tetrahydropyrimidin‐2‐thiones in satisfactory yields and with good diastereoselectivity. When aromatic aldehydes bearing electron‐withdrawing group were used in the reaction, the 4‐hydroxytetrahydropyrimidin‐2‐thione derivatives were obtained as the main product.