Spectroscopic and semiempirical investigation of the structural features of hetarylazo-5-isoxazolones tautomerism

Rageh, H.M.; Ibrahim, S. A.; Selim, M. A.; Alsoghier, Hesham M.

doi:10.1016/j.jscs.2015.01.007

Cited by 2 publications

(1 citation statement)

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“…Intramolecular N-H•••O hydrogen bonding study assisted by resonance for 1-ketone-2-arylhydrazones derivatives suggest that heterocyclic five member ring introduces geometrical constraint which hinders the strengthening of hydrogen bond [13]. Tautomerism and spectroscopic properties of some heteroarylazoisoxazolone dyes were studied earlier [14]. With these objects in view we focus on the synthesis and antimicrobial activity of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5one azo dyes.…”

Section: Introductionmentioning

confidence: 99%

Aqueous phase synthesis, crystal structure and antimicrobial activity of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-one azo dyes

Banpurkar¹,

Wazalwar²,

Perdih³

2018

Bull. Chem. Soc. Eth.

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3-Methyl-4H-isoxazol-5-one was synthesized at room temperature by simple stirring method from ethyl acetoacetate and hydroxylamine hydrochloride in aqueous medium and coupled with diazotized substituted amine to form series of 4-(substituted phenylazo)-3-methyl-4H-isoxazol-5-ones through green chemistry. All the compounds formed were characterized by IR, 1 H and 13 C NMR spectroscopy, MS and elemental analysis. Crystal structure of novel 4-(4-fluorophenylazo)-3-methyl-4H-isoxazol-5-one was determined by the X-ray diffraction. Antibacterial and antifungal activity was studied against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus pyogenus and Candida albicans, Aspergillus niger, Aspergillus clavatus, respectively. All synthesized compounds were found to be active against a gram-positive bacterium Staphylococcus aureus. Two compounds showed antifungal activity against Candida albicans close to standard greseofulvin.

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Section: Introductionmentioning

confidence: 99%