Synthesis and reactions of 4H-3,1-benzoxazin-4-one derivative bearing pyrazolyl moiety as antimicrobial and antioxidant agents

Ring opening of 4-aryl-2-phenyloxazol-5-one 1 with 2-aminobenzoic acid in acetic acid and n-butanol gave compounds 2 and 3, respectively. The 4H-3,1-benzoxazin-4-one derivative 4 was synthesized by refluxing of compound 2 in acetic anhydride. Then it reacted with different nitrogen nucleophiles such...

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Bibliographic Details
Published in:Synthetic communications 2019-11, Vol.49 (21), p.2840-2855
Main Authors: Haneen, David S. A., Gouhar, Rasha S., Hashem, Heba E., Youssef, Ahmed S. A.
Format: Article
Language:English
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Summary:Ring opening of 4-aryl-2-phenyloxazol-5-one 1 with 2-aminobenzoic acid in acetic acid and n-butanol gave compounds 2 and 3, respectively. The 4H-3,1-benzoxazin-4-one derivative 4 was synthesized by refluxing of compound 2 in acetic anhydride. Then it reacted with different nitrogen nucleophiles such as hydrazine hydrate, phenylhydrazine, cyclohexylamine, piperidine, ethylenediamine, ethanolamine, semicarbazide hydrochloride, cyanoacetohydrazide and methyl glycinate hydrochloride to give compounds 5-14 in order to study the behavior of these nucleophilic reagents on the performed ring system. All the structures of the newly prepared compounds were characterized by their IR, 1 H-, 13C-NMR and MS spectral data. Some of the synthesized compounds were screened for their antimicrobial and antioxidant activities. Compound 5 showed remarkable activity upon this screening.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2019.1646288