Synthesis of new heterocycles: Part XXVIII. Syntheses of condensed imidazoles

Nagarajan, K. ; Arya, V. P. ; Shenoy, S. J. ; Shah, R. K. ; Goud, A. N. ; Bhat, G. A. (1977) Synthesis of new heterocycles: Part XXVIII. Syntheses of condensed imidazoles Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 15 . pp. 629-634. ISSN 0376-4699

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Reaction of imino ethers Ila, lib, VI, IX and methylmercapto compounds Xlla and XIIc with aminoacetal, followed by treatment with HC1 affords imidazo[2,l-c][l,4]thiazine (IVa), imidazo[2,l-d][l,4]thiazepine (IVb), imidazo[2,l-a]pyrazine (VIII), imidazo[l,2-a]azepine (X), imidazo[l,2-a]imidazole (XHIa) and imidazo[l,2-a]pyrimidine (Xlllb) respectively. IVa and IVb are oxidized by acetic acid-hydrogen peroxide to the sulphones Va and Vb respectively; while nitration of XHIa and Xlllb gives the mononitro derivatives XlVa and XlVb. Treatment of 2-mercaptoimidazole with ethylene dibromide affords imidazo[2,l-b]thiazole (XVa),'which is further nitrated to the nitro compound XVb and then oxidized to the sulphone XVI. Several alicylic ketones and N-substituted piperidones have been condensed with histamine to give 7-spirocyclic imidazo[4,5-c]pyridines (XVIIIa-j, XX and XXI). Histamine and histidine are converted to their 5-nitro derivatives XVIId and XXV respectively. Interaction of XVIId with aromatic aldehydes yields imidazo[l,5-c]pyrimidines (XXIIIa-g).

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