Phosphoryl Chloride Mediated Synthesis of 5-Arylidene-2,4-Thiazolidinediones Derivatives via Aromatic Bisulfite Adducts
Sandeep Mohanty, Sandeep Reddy. G and Arun Chandra Karmakar
Affiliation: Process Research and Development, Dr. Reddy’s Laboratories Limited, API Plant, Bollaram-III, Plot No's 116, 126C, Survey No.157, S.V. Co-operative Industrial Estate, IDA Bollaram, Jinnaram Mandal, Medak District, Hyderabad 502325, Andra Pradesh, India.
Keywords: Aromatic aldehyde bisulfite adduct, phosphoryl chloride, thiazolidine-2, 4-dione.
The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with
thiazolidine-2, 4-dione to furnish 5-arylidene-2,4-thiazolidinedione’s has been investigated. This novel methodology was
applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione’s with POCl3 in
less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene)thiazolidine-2,4-dione and
5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.
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