الفهرس 
INTRODUCTIONOnly 14 pages are availabe for public view
 |  | from | 113 |  |  |
| | | from | 113 | | |
Abstract
The present investigation deals with the synthesis of some new be- nzoxazinonone and quinazolinone derivatives bearing a bulky moiety at position-3, in order to find out a role for the heterocyclic3-moiety, on the stability of benzoxazinonone nucleus and its reactivity towards some nuc- leophilic reagents.
This work involves synthesis and reactions of 2-(4-Chlorophenyl) benzo[d][1,3]oxazin-4-one (2). Thus, the reaction of anthranilic acid with p-chloro benzoyl chloride in the presence of acetic anhydride afforded 2 which reacted with nucleophiles as aniline, phenyl hydrazine, ,hydrazine hydrate, ammonium acetate , and glycine, to give 3, 4, 5, 6, 7 compounds respectively.
2-(4-Chloro phenyl)3H-quinazolin-4-one (6) and [2-(4-Chloro phe-nyl)4-oxo-4H-quinazolin-3-yl] acetic acid (7), used as precursors for many quinazoline compounds.
¬ Compound 6 reacted with phosphorus penta chloride and gave 4-Chloro-2-(4-Chloro phenyl) quinazolin (8) which reacted with hydrazine hydrate to give [2-(4-Chloro phenyl) quinazolin-4-yl] hydrazine (9). Also, compound 6 reacted with ethylchloroacetate to give [2-(4-Chloro phenyl) quinazolin-4-yloxy] acetic acid ethyl ester (10) which reacted with hydrazine hydrate to give [2-(4-Chlorophenyl) quinazolin-4yloxy] acetic acid hydrazide (11).
Compound 7 reacted with thionyl chloride and ammonium thiocyanate to give [2-(4-Chloro phenyl)-4-oxo-4H-quinazolin-3-yl] acetylisothiocyanate (13) which used as a precursor for many reactions. Isothiocyanate 13 reacted with nucleophiles like glycine, anthranilic acid, aniline, p-toloidine, p-anisidine, acetyl acetone, ethyl ac-
etoacetate, phenyl hydrazine, and gave 14, 15, 16, 17, 18 , 19, 20, 21, 22 compounds respectively.
{3-2-[(4-Chloro phenyl)-4-oxo-4H-quinazolin-3-ylmethyl]-2-phe-nyl5-thioxo-2,5dihydro-[1,2,4]triazol-1-yl} acetic acid (22) used as precursor for heterocyclic compounds which expected to have biological activity.
Compound (22) reacted with chloroacetic acid and gave{3-2-[(4-Chloro phenyl)-4-oxo-4H-quinazolin-3-ylmethyl]-2-phenyl-5-thioxo-2,5- dihydro [1,2,4]triazol-1-yl} acetic acid (23), which reacted with benzaldhyde and gave 2-{3-2-[(4-Chloro phenyl)-4-oxo-4H-quinazolin-3-ylmethyl]-2-phenyl-5-thioxo-2,5 dihydro-[1,2,4] triazol-1-yl}-3-phenyl-acrylic acid (24).
Also compound 22 reacted with methyl iodide and gave 2-(4-Chloro phenyl)-3-(5-methylsulfanyl-2-phenyl-2H-[1,2,4]triazol-3-ylmet-hyl 3H-quinazolin-4-one (25) which reacted with hydrazine hydrate and gave 2-(4Chloro phenyl)-3-(5-hydrazino-2-phenyl-2H-[1,2,4] triazol-3-ylmethyl)-3H-quinazolin-4-one (26).
The structure of all synthesized derivatives was established by:
1- Elemental analysis 2- I.R spectra
3- 1H NMR spectra 4- Mass spectra