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Highly Diastereoselective Synthesis of Dihydro‐benzoimidazo‐[1,3]‐thiazines via Electro‐oxidative Selenocyclization of Thioallyl Benzoimidazoles

Atreyee Halder, Kingshuk Mahanty, Debabrata Maiti, Suman De Sarkar

2021Chemistry - An Asian Journal29 citationsDOI

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.

Topics & Concepts

RegioselectivityStereocenterTandemStereoselectivityCombinatorial chemistryTolerabilityOxidative phosphorylationChemistryFunctional groupElectrochemistryStereochemistryMaterials scienceOrganic chemistryCatalysisEnantioselective synthesisPharmacologyBiochemistryElectrodePolymerMedicineAdverse effectComposite materialPhysical chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsOrganoselenium and organotellurium chemistry
Highly Diastereoselective Synthesis of Dihydro‐benzoimidazo‐[1,3]‐thiazines via Electro‐oxidative Selenocyclization of Thioallyl Benzoimidazoles | Litcius