Efficient, Stereoselective Approach to the Synthesis of 3-(1-Phenyl-2-(Z-styrylsulfonyl)-1H-imidazol-4-yl)-2H-chromen-2-ones

Abstract

Reaction of phenyl acetylene with 3-(1-aryl-2-mercapto-4-imidazolyl)-2H-1-benzopyran-2-ones (4) in the presence of sodium hydroxide in absolute ethanol led to the formation of 3-(1-phenyl-2-(Z-styrylthio)-1H-imidazol-4-yl)-2H-chromen-2-ones (6) in excellent yields. These, on further oxidation with H₂O₂/AcOH, gave the corresponding sulfones (7) with retention of stereochemistry.

Keywords:

• 3-(2-Mercapto-1-phenyl-1H-imidazol-4-yl)-2H-chromen-2-ones
• phenylacetylene
• styryl sulfides
• sulfones

ACKNOWLEDGMENT

We are grateful for financial support from the Council of Scientific and Industrial Research (CSIR), New Delhi, Project No. 01 (2062) 06/EMR-II.