A facile access to the synthesis of functionalised unsymmetrical biaryls from 2H-pyran-2-ones through carbanion induced C–C bond formation

Abstract

A convenient synthesis of highly functionalised biaryls 3 and 6 has been delineated through carbanion induced C–C bond formation from 6-aryl-3-cyano-4-substituted-2H-pyran-2-ones (1, 4) and acetone. Extension of this reaction, using aromatic ketones led to (4,6-diarylpyran-2-ylidene)acetonitrile (7) in lieu of the anticipated 2,4-diaryl-6-methylthiobenzonitrile (8). The structure of 2-methyl-6-methylthio-4-(3,4-methylenedioxyphenyl)benzonitrile (3f) was ascertained by single crystal X-ray diffraction analysis and displayed a variety of weak interactions, responsible for the stability and packing of the molecule in the crystalline state.