Synthesis and reactions of 6-acetyl-7-hydroxy-4-methyl coumarin

ABSTRACT

Perkin condensation of 2, 4 diacetyl resorcinol with acetic anhydride and sodium acetate gave 6-acetyl-7-hydroxy-4-methyl coumarin [I]. Nitration of coumarin [I], then reduction followed by diazotization and coupling gave 3-azocoumarin derivative [V]. Alkylation of I followed by cyclization with anthranilic acid gave 2-[7/[6/acetyl-4-methyl] coumarinoxy] methyl-[4H] 3, 1-benzoxazin-4-one [VII]. The behavior of coumarin I towards bromination in different solvents, Claisen and Grignard reaction were studied and gave compounds [VIII-XII]. The structures of the products were confirmed by elemental analysis, IR and 1H-NMR spectroscopy