Brønsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C−N Bond Cleavage; One‐Step Synthesis of 2‐Substituted Benzothiazoles
Srabani Maity, Arnab Roy, Surajit Duari, Subrata Biswas, Subrata Biswas, Asma M. Elsharif, Srijit Biswas, Srijit Biswas
Abstract
Abstract We have developed a Brønsted acid mediated synthetic method to directly cleave stable amide C−N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2‐substituted benzothiazole derivatives have been synthesized in one pot employing 2‐aminothiophenol as nucleophile.
Topics & Concepts
ChemistryBenzothiazoleNucleophileAmideAmine gas treatingReactivity (psychology)Bond cleavagePeptide bondAlcoholBrønsted–Lowry acid–base theoryNucleophilic substitutionCleaveNucleophilic additionOrganic chemistryCombinatorial chemistryMedicinal chemistryCatalysisEnzymeAlternative medicinePathologyMedicineAdvanced Synthetic Organic ChemistryChemical synthesis and alkaloidsChemical Synthesis and Analysis