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

Authors : Hülya ÇELİK ONAR, Didem ERDOĞAN

Pages : 134-139

Doi:10.16984/saufenbilder.503046

View : 18 | Download : 9

Publication Date : 2020-02-01

Article Type : Research Paper

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 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 insert ignore into journalissuearticles values( 7-Hydroxy-4-methyl-8-[insert ignore into journalissuearticles values(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 insert ignore into journalissuearticles values( 2-insert ignore into journalissuearticles values(2’-Hydoxy-5-methyl coumarin-1-yl);-2,3-dihidro quinazoline-4insert ignore into journalissuearticles values(1H);-on );. Our compounds are thought to exhibit biological activity. Their structures were identified by IR, 1 H NMR,  13 C NMR , MS analysis.
Keywords : Schiff base, coumarin, Pechmann reaction, Duff reaction, 6 amino 1, 4 benzodioxane