Synthesis and characterization of novel 2-oxo-4-((4-(3-oxomorpholino)phenyl)amino)-2H-chromene-3-carbonitrile derivatives

ABSTRACT

A highly functionalized heterocyclic library were synthesized, and characterized by common spectroscopic methods. This novel synthetic rout involves nucleophilic substitution reaction of 3-cyano-4chloro coumarin with 4-(4-aminophenyl)morpholin-3-one in the presence of base and methanol as a solvent in good yield and high purity. Key starting material 4-(4-aminophenyl)morpholin-3-one synthesized from aniline. The reaction of aniline with ethylene oxide gives INT-1 which on reaction with Chloroacetyl chloride yield INT-b. Nitration of INT-b gives INT-c, which on reduction with Sn/HCl gives int-D. Further INT-3 was synthesized from 4-hydroxy coumarin. The Vilsmeier-haack reaction of 4-hydroxy coumarin gives INT-01 which on reaction with hydroxylamine hydrochloride and sodium acetate furnished INT-03. All the synthesized compound of libraries characterized using ¹H NMR, Mass, and IR spectroscopic technique.