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Synthesis of Novel Thiazolidin‐4‐ones and Thiazinan‐4‐ones Analogous to Rosiglitazone
Author(s) -
Neves Adriana M.,
Campos José C.,
Gouvêa Daniela P.,
Berwaldt Gabriele A.,
Goulart Taís B.,
Avila Cinara T.,
Machado Pablo,
Zimmer Geórgia C.,
Cunico Wilson
Publication year - 2019
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.3402
Subject(s) - chemistry , rosiglitazone , benzaldehyde , mass spectrometry , nuclear magnetic resonance spectroscopy , organic chemistry , combinatorial chemistry , medicinal chemistry , catalysis , chromatography , biochemistry , receptor
This work reports the synthesis of thiazolidin‐4‐ones and thiazinan‐4‐ones analogous to rosiglitazone, a potent antidiabetic drug. The desired compounds were synthesized with moderate to good yields by one‐pot reactions between different primary amines, mercaptoacetic or mercaptopropionic acids, and the 4‐(2‐(methyl(pyridin‐2‐yl)amino)ethoxy)benzaldehyde. The cyclocondensation reactions were carried out for 20 h, and all the products were characterized by 1 H and 13 C nuclear magnetic resonance spectroscopy, mass spectrometry, and one example by X‐ray diffraction.