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Heterocyclic compounds from 4 h ‐3,1‐benzoxazin‐4‐one derivatives as anticancer agent
Author(s) -
AbdelRahman Taha M
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420703
Subject(s) - chemistry , ethyl chloroacetate , ethyl acetoacetate , hydrazine (antidepressant) , nucleophile , adduct , thio , organic chemistry , benzoic acid , hydrate , medicinal chemistry , ammonium acetate , high performance liquid chromatography , chromatography , catalysis
Behaviour of 2‐(4‐oxo‐4 H ‐benzo[ d ][l,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 elec‐trophiles 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 thio‐glycolic 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.