Abstract
The behavior of 2-ethoxy-(4H)-3,1-benzoxazin-4-one (1) towards nitrogen nucleophiles, e.g. ethanolamine, aromatic amines (namely: p-toluidine, p-anisidine, p-hydroxyaniline, o-hydroxyaniline, o-bromoaniline, o-phenylenediamine, p-phenylenediamine, o-tolidinediamine) p-aminobenzoic acid, glucosamine hydrochloride, 2-aminonicotinic acid, 1-naphthalenesulfonic acid hydrazide, n-decanoic acid hydrazide, benzoic acid hydrazide, semicarbazide, aminoacids (e.g. D,L-alanine, L-asparagine, L-arginine) and derivatives of 2-aminothiodiazole has been investigated. The behavior of the benzoxazinone towards a selected sulfur nucleophile, L-cysteine, has also been discussed. Formation of an amidine salt as a reaction intermediate has been assumed. The effect of solvent in some reactions has been elucidated. The structures of all the novel quinazoline and quinazolinone derivatives, obtained by heterocyclic ring opening and ring closure were inferred by the IR, MS as well as 1H-NMR spectral analysis. Moreover, the antimicrobial potential of some of the new synthesized derivatives has been evaluated.
Highlights
The behavior of 2-ethoxy-(4H)-3,1-benzoxazin-4-one (1) towards nitrogen nucleophiles, e.g. ethanolamine, aromatic amines p-aminobenzoic acid, glucosamine hydrochloride, 2-aminonicotinic acid, 1-naphthalenesulfonic acid hydrazide, n-decanoic acid hydrazide, benzoic acid hydrazide, semicarbazide, aminoacids (e.g. D,L-alanine, L-asparagine, L-arginine) and derivatives of 2-aminothiodiazole has been investigated
This special reactivity allows this class of compounds to be useful as antimicrobial [1], anti-platelet aggregation [2], human leukocyte elastase inhibitors [3], receptor agonist active [4], receptor antagonist active [5,6,7,8,9], pesticides [10], tissue culture protective and in vivo
Pharmaceuticals 2011, 4 model of neurodegeneration [11] and improve the umbilical vein endothelial cells [12]. We report both the uses of 2-ethoxy-(4H)-3,1-benzoxazin-4-one (1, Scheme 1) in the synthesis of some quinazolinone derivatives and the screening of antimicrobial activity of some of the newly synthesized derivatives against Gram-negative and Gram-positive bacteria as well as fungi by means of the disc diffusion method
Summary
3,1-Benzoxazin-4-ones can be considered as semiacid anhydrides which undergo many of the reactions of true acid anhydrides, but at a slower rate. This special reactivity allows this class of compounds to be useful as antimicrobial [1], anti-platelet aggregation [2], human leukocyte elastase inhibitors [3], receptor agonist active [4], receptor antagonist active [5,6,7,8,9], pesticides [10], tissue culture protective and in vivo. We report both the uses of 2-ethoxy-(4H)-3,1-benzoxazin-4-one (1, Scheme 1) in the synthesis of some quinazolinone derivatives and the screening of antimicrobial activity of some of the newly synthesized derivatives against Gram-negative and Gram-positive bacteria as well as fungi by means of the disc diffusion method
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