Synthesis, reactions and antifungal agents of 2-[1-benzoylamino-2-[naphthyl-and/or 2 2-furyl] vinyl 4-H-3,1 benzoxazin-4-ones derivatives

The reactivity of on N-[2-naphthalen-1 or 2-furan-2]-yl-1-[4-oxo-4H-benzo[d] [1, 3]oxazin- 2-yl]-vinyl]-benzamide [3a, b] towards the nitrogen and carbon nucleophiles, led to the direct formation of heterobicyclic nitrogen compounds. Structure of the newer synthesized products [3-25] was confirmed by elemental analysis as well as by studying of their spectral data [IR. [1]H-NMR and [B]C-NMR]. Some of the target selected synthesized compounds showed remarkable anifungal activity

Synthesis and behaviour of 2-carboxyvinyl-6,8-dibromo-4H-3,1- benzoxazin-4- one towards nitrogen, carbon, and sulphur nucleophiles

3-[6, 8-DIBROMO-4-oxo-4H-benzo[d][1, 3] oxazin-2-yl]- acrylic acid [1] was synthesized and allowed to react with some nitrogen nucleophiles namely, 4-methylaniline, hydroxylamine hydrochloride, ethanolamine and glycine afforded 3-substituted quinazolinones 2-5. while with isobutylamine and benzylamine gives benzamide derivatives 6a and 6b. Compound 3 was subjected to acylation and alkylation resulting in 7 and 8, respectively. Also, compound 4 was utilized to alkylate some aromatic systems namely, 2-naphthol and benzamide to give 9a and 9b. Treatment of benzoxazinonone 1 with ophenylenediamine in different solvents under different conditions: furnished a substituted benzamide 10 and 3-substituted-quinazolinone 11. Benzoxazinone 1 was converted to 4[3H]-quinazolinone 12 by treatment with formamide and/or ammonium acetate which was alkylated with ethylchloroacetate yielded 13, which in turn reacted with hydrazine hydrade produced the hydrazide 14. Interaction of compound 1 with hydrazine hydrate gave the unexpected product fused quinazolinone 15, which was confirmed by its interaction with acid chlorides namely, acetyl and benzoyl chloride affording 16 and 17, respectively. Oxazinone ring cleavage occurred by the use of active methylene containing compounds under different conditions, thioglycolic acid, thiophenol, and thiosemicarbazide yielded 18 - 22. An interesting heterocyclization occurred by treatment of 22 with diethylmalonate producing the pyrimidindione 23