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

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 compound 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-dihidro-1,4-benzodioxin-6-yl)iminomethyl]-2H-1-benzopiran-2-on) is obtained as a coumarin schiff base, ring closure was observed at 4 (2-(2’-Hydoxy-5-methyl coumarin-1-yl)-2,3-dihidro quinazoline-4(1H)-on). 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,

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