Regioselective N-Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate-Catalyzed Substitution of Alcohols and Alkyl Group Migrations
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Data
2022-02-15
Autores
Duari, Surajit
Biswas, Subrata
Roy, Arnab
Maity, Srabani
Mishra, Abhishek Kumar
de Souza, Aguinaldo R. [UNESP]
Elsharif, Asma M.
Morgon, Nelson H.
Biswas, Srijit
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Resumo
A catalytic synthetic strategy has been developed combining two protocols, such as, direct nucleophilic substitution of alcohols followed by X- to N- alkyl group migration (X=O, S) to access N-functionalized benzoxazolones, benzothiazolethiones, indolinone, benzoimidazolethiones, and pyridinones derivatives. Methyl trifluoromethanesulfonate (MeOTf) was found to catalyze the reaction, which revealed the catalytic property of MeOTf. A mechanism was established through experiments as well as DFT calculations wherein the −OH group of alcohols were converted to the corresponding −OMe groups and in situ generated TfOH. The −OMe groups produced underwent TfOH catalyzed −X alkylation (X=O, S) of the heterocycles followed by −X- to −N-alkyl group migrations in a single step. (Figure presented.).
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Alcohols, Alkylation, Heterocycles, MeOTf Catalyst, Nucleophilic Substitution, Rearrangement
Como citar
Advanced Synthesis and Catalysis, v. 364, n. 4, p. 865-872, 2022.