Synthesis, Stereochemistry and Antimicrobial Activity of Some Novel Flavanone-hydrazono-thiazolidin-4-ones from Flavanones

摘要

The synthesis of four novel compounds, (i) E-2-([2-(4-methoxyphenyl)chroman-E-4-ylidene]hydrazono)thiazolidin-4-one (4a), (ii) E-2-{[2-(4-methoxyphenyl)chroman-Z-4-ylidene]hydrazono}thiazolidin-4-one (5a), (iii) E-2-{ [2-(pheriyl)chroman-E-4-ylidene]hydrazono}-thiazolidin-4-one (4b) and (iv) E-2-{[2-(phenyl)chroman-Z-4-ylidene]hydrazono}thiazolidin-4-one (5b) from 4'-methoxy flavanone (1a) in (i) and (ii) and from flavanone (1b) in (iii) and (iv) via the reaction of respective thiosemicarbazones (2a) and (2b), with chloroacetic acid and sodium acetate in acetic acid is described. Structural assignment, stereochemistry and biological assays are discussed.