Synthesis of Nitrogen-Containing Chalcone Via One-Pot Three-Component Reaction: Part IV

Abstract

The mannich reaction is one of the most important C-C bond formation methods in organic   synthesis. The mannich-reaction is employed in the   organic synthesis of natural compounds like for instance peptides-nucleotides-antibiotics and alkaloids. Other application are in agrochemicals such as plant growth regulators, paint and other polymer chemistry, catalysts and cross linking. The mannich reaction is also used in synthesis of medicinal compounds. The compound 4-Hydroxy-4'-methoxychalcone was prepared by reacting 4-hydroxybenzaldehyde with 4-methoxyacetophenone. The aminomethylation of this chalcone was accomplished by reaction with formaldehyde and suitable amine in acetonitrile to obtain 4-hydroxy-4'-methoxy-3,5-bis-dimethylaminomethylchalcone(2) 4-hydroxy-4'-methoxy-3, 5-bis-pyrrolidinomethylchalcone(3) and4-hydroxy-4'-methoxy-3, 5-bis-piperdinomethylchalcone(4). The products were purified by column and thin layer chromatography and were identified along with their intermediates by spectroscopic methods: UV, IR, and NMR and mass spectrometry.