Synthesis and Antimicrobial activity of 1-(3-amino-5-chloro-2, 3-dihydro-1-benzofuran-2-yl) ethan-1-one [2, 1-b]-furan and their derivatives

Abstract

The current study is focused on the conversion of 2- chlorosalicylaldehyde into its oxime which was then converted into 5-chloro-2-hydroxy-benzonitrile 1, a key starting material for the present synthetic work. The nitrile 1 on reaction with chloroacetone/phenacyl bromide/4-chlorophenacyl bromide in anhydrous acetone and potassium carbonate gave 2-acyl-3- amino-5-chlorobenzofuran (2a-c). Acetylation of compounds 2a-c furnishes 2-acyl-3acetamido-5- chlorobenzofuran (3a-c). Compounds 3a-c on further treatment with hydrazine hydrate undergo ring closure producing 3-amino-8- chloro-2, 4-dimethyl-3, 4-dihydro [1] benzofuran [3, 2- d] pyrimidin-4-ol (4a-c). The synthesised compounds were characterised by spectral and analytical data and screened for antibacterial and antifungal activity.