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Triethylamine‐Catalyzed Domino Reactions of 1,3‐Thiazolidinedione: A Facile Access to Functionalized Dihydrothiophenes
Author(s) -
Sun Jing,
Xia ErYan,
Zhang LiLi,
Yan ChaoGuo
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900845
Subject(s) - triethylamine , domino , chemistry , malononitrile , catalysis , thiazolidinedione , combinatorial chemistry , ring (chemistry) , organic chemistry , medicinal chemistry , diabetes mellitus , medicine , type 2 diabetes , endocrinology
In the presence of triethylamine as base catalyst, aromatic amines have successfully been used as substrates in the domino reactions of 1,3‐thiazolidinedione, malononitrile, and aromatic aldehydes. Through a domino ring‐opening/recyclization process of 1,3‐thiazolidinedione, a series of polysubstituted dihydrothiophenes in the trans configuration have been synthesized in high yields. Dihydrothiophene derivatives can be converted efficiently into the corresponding thiophenes by oxidation with DDQ under mild conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)