A concise synthesis of 2-alkenyl-3-phenyl-4H-chromen-4-ones via novel C-C bond formation using sulfone as potential intermediate

摘要

A new methodology has been designed for the synthesis of some non-natural 2-alkenyl-3-phenyl-4H-chromen-4-ones of potential biological importance. The strategy makes use of appropriately substituted heteroaryl sulfone as the potent intermediate. An ambident nucleophile has been generated by treating the sulfone with NaH in DMF followed by its alkenylation, using a suitable alkenyl bromide, to yield a product which on reduction with sodium-amalgam gives the desired target molecule. Using this strategy, twelve new analogs of the target molecule have been successfully synthesized. These newly synthesized 3-phenyl-4H-chromen-4-ones are good candidates for exploration of biological activity as they all contain lipophilic chains, normally present in drug like molecules.