Highly Efficient One-pot Synthesis, Antimicrobial and Docking Studies of Newer β-amino Carbonyl Derivatives Catalyzed by Silica Sulfuric Acid

Mannich reaction was applied between 4-fluorobezaldehyde, selected acetophenone and several anilines, catalyzed by silica sulfuric acid for the synthesis of β-amino carbonyl derivatives. Reaction time and yield of the products depended on the nature of acetophenone and aniline subsituents. Using aliphatic amines instead of aromatic amines under same reaction conditions, afforded aldol condensation products without yielding the expected β-amino ketones. Replacing the acetophenone derivatives with rhodanine yielded 5-(4-fluorobenzylidene)-thioxothiazolidin-4-one. Using 2-aminothiophenol instead of the aniline derivatives, 2-(4-fluorophenyl)benzothiazole was obtained without isolation of the expected (mercaptophenylamino)-1-(4-substitutedphenyl)propan-1-ones. A proposed reaction mechanism was suggested. Docking studies were designed to gain clear picture of the high active compound(s). A model of high active molecules was mapped for the antimicrobial screening and compared with least active compound(s). (doi: 10.5562/cca1983)