Utilization of 2-substituted 3, 1-benzoxazin-4-ones in synthesis of some quinazoline annulated derivatives

In this study, a new series of quinazoline and their annulated derivatives have been synthesized. A number of quiazolinone derivatives substituted at position-3 were prepared from 3, 1-benzoxazinone by the treatment of 3,1-benzoxazinone with different nitrogen nucleophiles such as, hydrazine hydrate...

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Bibliographic Details
Published in:Synthetic communications 2020-03, Vol.50 (6), p.879-892
Main Authors: Abd-Alaziz, Asmaa M., Sallam, Hanan A., Youssef, Ahmed S. A., El-Naggar, Abeer M.
Format: Article
Language:English
Subjects:
3,1-Benzoxazinone
Aldehydes
Derivatives
Hydrazines
NMR
Nuclear magnetic resonance
Nucleophiles
pyrazoloquinzolinone
Schiff's bases
Substitutes
Synthesis
triazinoquinazolinone
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Summary:In this study, a new series of quinazoline and their annulated derivatives have been synthesized. A number of quiazolinone derivatives substituted at position-3 were prepared from 3, 1-benzoxazinone by the treatment of 3,1-benzoxazinone with different nitrogen nucleophiles such as, hydrazine hydrate, phenylhydrazine, ethanolamine, and cyano acetohydrazide afforded the quinazolinone derivatives 7-11. The reaction of hydrazide derivative 5 with aromatic aldehydes gave the Schiff's bases derivative 16a-c. Some of the synthesized compounds were tested against the breast cancer cell line (MCF-7). The structures of all the newly synthesized compounds were established based on IR, 1 H, 13 C NMR, mass spectral data, and elemental analyses.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1725574