Synthesis of novel 8-formyl-7-hydroxy-4-methylcoumarin derivatives

Abstract

This study was initiated by 7-hydroxy-4-methylcoumarin 1 synthesis according to the Peckmann reaction with resorcinol and ethylacetoacetate. This compound was converted into 8-formyl-7-hydroxy -4- methylcoumarin 2 by the Duff reaction. This aldehyde obtained was reacted with 6-amino-1,4-benzodioxane and 2-amino benzamide, which have their specific biological activities, to synthesize the original two novel compounds. While 3 (7-Hydroxy-4-methyl-8-[(2,3-dihydro-1,4-benzodioxin-6- yl)iminomethyl]-2H-1-benzopyran-2-one) is obtained as a coumarin schiff base, ring closure was observed at 4 (2-(2’-Hydoxy-5-methyl coumarin-1-yl)-2,3-dihydro quinazoline-4(1H)-one). Our compounds are thought to exhibit biological activity. Their structures were identified by IR, 1H NMR, 13C NMR, MS analysis.Keywords: Schiff base, coumarin, Pechmann reaction, Duff reaction, 6-amino-1,4-benzodioxane and 2- amino benzamide.