RESUMEN
Pyrazoline, isoxazoline. pyrimidine and pyrimidinethione derivatives have been reported as highly potent agent against fungi and bacteria[1-6] As a result of our interest to prepare a new and microbial active azoles [7-10], we report here the synthesis of new azoles and pyrimidinone derivatives starting from benzo- [G] -4-chloro-l,2-dihydroquinolinoquinone-3-carboxaldehyde [2]. Formylation of benzo-[G] 1,2,3,4-tetrahydroquinoline 4,5, 10-trione [l][11] via Vilsmeier reagent [POC13/DMF] afforded benzo-[G]-4-ch1oro-l, 2-, dihydroquinolinoquinone-3-carboxaldehyde [2]. The 1HNMR spectra of [2] have shown a singlet signal at sigma 10.0 pmm due to proton of the formyl group and its mass spectra showed clear isotopic effect. Condensation of the formylated compound [2] and 4-substituted acetophenone in alkaline ethanol produced the corresponding alpha, beta unsaturated compounds [3 a-c].[1]H NMR. Spectra of the compourds [3a-c] showed the disappearance of the formyl proton at sigma10.0 ppm, meanwhile two doublets are observed around sigma 5 .8-6.2 ppm, for protons at conjugated double bond. Cycloaddition reaction of [3a-c] and hydrazine hydrate in presence of acetic acid, phenylhydrazine in catalytic amounts of piperidine, hydroxylamine hydro chloride in alkaline ethanol, urea and/or thiourea in presence of 5NHC1 afforded the corresponding pyrazolines [4a,b; 4d, e and 4g, h], isoxazolines [4c; 4f and 4i] pyrimidinone [5a; 5c and 5e] and/or pyrimidinethione [5b; 5c and 5f], respectively. The chemical structure of these new compounds were established based on IR, [1] H-NMR and mass spectra, as well as their elemental analysis [c.f. tables 1,2]