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Highly Diastereoselective Synthesis of Dihydro-benzoimidazo-[1,3]-thiazines via Electro-oxidative Selenocyclization of Thioallyl Benzoimidazoles
Authors:Atreyee Halder  Kingshuk Mahanty  Debabrata Maiti  Dr Suman De Sarkar
Institution:Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246 West Bengal, India
Abstract:The current methodology reveals a green and proficient electro-oxidative tandem selenocyclization of thioallyl benzoimidazoles manufacturing selenylated dihydro-benzoimidazo-thiazine derivatives. Both C−Se and C−N bond formation were achieved via this mild protocol which exhibits good functional group tolerability affording an extensive range of substrate scope up to 96% isolated yields. Complete control over the regioselective formation of the six-membered heterocycle and stereoselective construction of the contiguous stereocenters was established. The practical electrochemical method operates in an undivided cell at ambient temperature without using any metal and external chemical oxidant.
Keywords:Electrosynthesis  Selenylation  Thiazine  Diastereoselective  Annulation
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