Alkylation by enamines for synthesis of some heterocyclic compounds

Abstract EN

Compounds of 4-phenyl-3-butene-2-one (1) and 4-(4-chlorophenyl)-3-butene-2-one (2) were prepared by reaction of benzaldehyde or 4-chlorobenzaldehyde with acetone.

Also 1-, 3 diphenyl-2-chloropropene-1-one (3) was synthesized from the reaction of benzaldehyde with 2-chloroacetophenone through Claisen-Shmidt condensation.

The substituted Δ1 (9)-octalone-2 (4, 5) was prepared by reaction of the compounds (1and2) with cyclohexanone through Michael addition followed by aldol condensation.

Compounds (4, 5) were reacted with alkyl halide, as 2-chloroacetophenone or 1,3-diphenyl-2-chloropropene-1-one (3), via enamines formation which then hydrolyzed to give compounds (6-9).

Compounds (6, 7) were reacted with hydrazine, urea and thiourea to afford compounds (10-15).

The structures of all synthesized compounds were confirmed by available physical and spectral means.