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

Year 2020, Volume: 24 Issue: 1, 134 - 139, 01.02.2020

Hülya Çelik Onar , Didem Erdoğan

https://doi.org/10.16984/saufenbilder.503046

Cited By: 1

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 (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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