egioselective N-Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate-Catalyzed Substitution of Alcohols and Alkyl Group Migration

Autor(es)

Duari, Surajit ^[1] ; Biswas, Subrata ^[1] ; Roy, Arnab ^[1] ; Maity, Srabani ^[1] ; Mishra, Abhishek Kumar ^[2] ; Souza, Aguinaldo R. ^[3] ; Elsharif, Asma M. ^[4] ; Morgon, Nelson H. ^[5] ; Biswas, Srijit ^[1]

Afiliação do(s) autor(es)

^[1] Univ Calcutta, Dept Chem, 92 APC Rd, Kolkata 700009, W Bengal - India

^[2] CSIR Cent Drug Res Inst, Dept Med & Proc Chem, Lucknow 226031, Uttar Pradesh - India

^[3] Sao Paulo State Univ, Dept Chem, Sch Sci, BR-17033360 Bauru, SP - Brazil

^[4] Imam Abdulrahman Bin Faisal Univ, Dept Chem, POB 1982, Dammam 31441 - Saudi Arabia

^[5] Univ Estadual Campinas, Dept Phys Chem, Inst Chem, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ADVANCED SYNTHESIS & CATALYSIS; v. 364, n. 4, p. 865-872, FEB 15 2022.
• Citações Web of Science: 0

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. (AU)

• Processo FAPESP: 19/12294-5 - Cálculos teóricos de espectros eletrônicos (UV-Vis, fluorescência e dicroísmo circular) de moléculas de interesses farmacológico e aplicado
• Beneficiário: Nelson Henrique Morgon
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 13/08293-7 - CECC - Centro de Engenharia e Ciências Computacionais
• Beneficiário: Munir Salomao Skaf
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs