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Synthesis of novel thiazolobenzimidazoles
Abstract
For the synthesis of novel thiazolo[3,2-a]benzimidazol-3-ones and thiazolo[3,2-a]benzimidazoles, two methods have been developed which afforded the target compounds in relatively good yields by a pot process. The reaction between 2-mercapto-1H-benzimidazoles, acetophenone derivatives and 4- methylcyclohexanone in acid medium gave the tricyclic and tetracyclic benzimidazole compounds. We have also studied the flexibility of the position-7 of the thiazolobenzimidazoles by introducing the nitro and the methyl group. All compounds were characterized by means of 1H, 13C NMR and mass spectroscopy. The structures of the isomers of the 3-(2-methoxyphenyl)-6-nitrobenzo [4,5] imidazo[2,1-b]thiazole 14a, separated by a selective crystallization from diethyl ether were confirmed by RX analysis.
Keywords: Thiazolo[3,2-a]benzimidazol-3-ones, thiazolo[3,2-a]benzimidazoles, hologenoesters, 2- mercaptobenzimidazoles, tetrahydrobenzo[d]benzo[4,5]imidazo[2,1-b]thiazoles, flourene.
