Synthesis, spectral and biological evaluation of some new heterocyclic derivatives incorporating dihydroanthracene moiety

The reaction of anthrone 1 with 4-aminoantipyrine and thiosemicarbazide afforded 4-(anthracen-9(10H)-ylideneamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 2 and anthracen-9(10H)-one thiosemicarbazone 5, respectively. Oxidation of compound 2 with potassium permanganate gave 4-(anthracen-9(10H)-ylideneamino)-1-methyl-3-oxo-2-phenyl-2,3-dihydro-1H pyrazole-5-carboxylic acid 3 which on reaction with o-phenylenediamine gave 4-(anthracen-9(10H)-ylideneamino)-5-(1H-benzimidazol-2-yl)-1-methyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one 4. Furthermore, compound 5 was condensed with different substituted phenacyl bromide to give a series of 2-(anthracen-9(10H)-ylidenehydrazono)-5-substituted-2,3-dihydro-1H-thiazole 6a–g. Compound 5 also reacted with chloroacetic acid affording 2-(anthracen-9(10H)-ylidenehydrazono)thiazolidin-4-one 7. The structures of all the products have been determined by elemental analysis and spectral studies. All compounds have been screened for their antibacterial and antifungal studies. The results are summarized in Table 1 and Table 2.