Artículos de revistas
Regioselective N-Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate-Catalyzed Substitution of Alcohols and Alkyl Group Migrations
Fecha
2022-02-15Registro en:
Advanced Synthesis and Catalysis, v. 364, n. 4, p. 865-872, 2022.
1615-4169
1615-4150
10.1002/adsc.202101196
2-s2.0-85122894665
Autor
University of Calcutta
CSIR-Central Drug Research Institute
Universidade Estadual Paulista (UNESP)
P.O. Box 1982
Universidade Estadual de Campinas (UNICAMP)
Institución
Resumen
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.).