Synthesis and Characterization of New Coumaran-2-one Derivative Through Cyclic Esterification of α-Aminonitrile Compound

The synthesis of new compound 3-{[3-(4-hydroxyphenyl)-5-mercapto-4H-1,2,4-triazol-4-yl]amino}benzofuran-2(3H)-one was achieved by cyclic esterification of α-amino acid which is derived from acid hydrolysis of α-aminonitrile compound using 50% H2SO4. 2-(2-Hydroxyphenyl)-2-{[3-(4-hydroxyphenyl)-5-mercapto-4H-1,2,4-triazol-4-yl]amino}acetonitrile (α-aminonitrile) was synthesized through three-competent one-pot reaction (Strecker reaction), that aldehyde, amine and potassium cyanide were mixed in glacial acetic acid as solvent. The amine used in this reaction was synthesized from several steps to introduce a heterocyclic triazole which is an important part in the final structure beside the heterocyclic benzofuran-2-one. Two cyclization reactions were involved in synthesis of our target coumaran-2-one derivative, the first was in the triazole cyclization and the second was in the esterification reaction (lactonization). The structures of the new compounds were characterized by elemental analysis, infrared, and nuclear magnetic resonance spectroscopy.