One-pot three-component synthesis of novel phenyl-pyrano-thiazol-2-one derivatives and their anti-diabetic activity studies

Abstract

An easy and rapid synthetic approach for the synthesis of phenyl-pyrano-thiazol-2-one derivatives using base catalysed one-pot three-component reaction between substituted aromatic aldehyde, N-methyl-1-(methylthio)-2-nitroethamine (NMSM) and thiazolidinedione is reported. Among the bases tested, piperidine was proven to be the most efficient organo-base catalyst, when ethanol was used as a solvent. The product was obtained in good yields and confirmed using FT-IR, NMR and mass spectroscopic techniques. The electron withdrawing group substituted product was obtained in higher yield compared to the electron donating group substituted product. The strategy used involved mild reaction conditions, shorter reaction time and easy isolation of products. The reaction sequence involved Knoevenagel condensation, Michael addition followed by intramolecular O-cyclization.

Keywords

• Three-component synthesis
• Knoevenagel condensation
• Michael addition
• O-cyclization