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Heterocyclic compounds from 4h-3,1-benzoxazin-4-one derivatives as anticancer agent

✍ Scribed by Taha M Abdel-Rahman

Publisher: Journal of Heterocyclic Chemistry
Year: 2005
Tongue: English
Weight: 194 KB
Volume: 42
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570420703

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✦ Synopsis

Behaviour of 2-(4-oxo-4H-benzo [d][1,3]oxazin-2-yl)-benzoic acid (1) towards nitrogen nucleophiles namely, hydrazine hydrate, in different solvents, ammonium acetate, and o-phenylenediamine has been investigated to give aminoquinazolin-4-one, benzotriazepinone, spiro-type compound, and nitrogen bridgehead compounds 3-5, respectively. Also, reactivity of the aminoquinazolin-4-one 2 towards carbon electrophiles such as ethyl acetoacetate, ethyl phenylacetate, ethyl chloroacetate, and aromatic aldehydes has been discussed. Reaction of Schiff's base 8 with sulfur nucleophiles namely o-aminothiophenol and/or thioglycolic acid afforded Michael type adducts. Structural assignments, of products 1-24 have been confirmed by elemental analysis and spectral data ( 1 H-and 13 C -NMR and MS fragmentation). The bioassay indicates that some of the target compounds obtained have good selective anticancer activity.

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