title: Three Component Divergent Reactions: Base-Controlled Amphiphilic Synthesis of Benzimidazole-Linked Thiazetidines and Fused Thiadiazines.
abstract: A divergent reaction of 2-aminobenzimidazole with isothiocyanates and dihalomethanes has been developed for the selective synthesis of benzoimidazothiazetidine and benzoimidazothiadiazine. A single-pot reaction of 2-aminobenzimidazole in the presence of sodium hydride delivers benzoimidazothiazetidine, whereas triethylamine promotes the formation of benzoimidazothiadiazine via a sequential stepwise fashion. The reaction sequence involves the initial formation of thiourea followed by regioselective nucleophilic addition and intramolecular ring-closing with dihalo electrophiles. The observed regioselectivity of this reaction is governed by the nature of bases and the reaction sequence.
authors: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan, ROC.
authors: Manikandan
authors: M
authors: Selvaraju
authors: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan, ROC.
authors: Sandip
authors: S
authors: Dhole
authors: Department of Applied Chemistry, National Chiao-Tung University , 1001 Ta-Hseuh Road, Hsinchu 300-10, Taiwan, ROC.|Department of Medicinal and Applied Chemistry, Kaohsiung Medical University , 100 Shih-Chuan First Road, Kaohsiung 807-08, Taiwan, ROC.
authors: Chung-Ming
authors: CM
authors: Sun