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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
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]
Total Authors: 9
Affiliation:
[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
Total Affiliations: 5
Document type: Journal article
Source: ADVANCED SYNTHESIS & CATALYSIS; v. 364, n. 4, p. 865-872, FEB 15 2022.
Web of Science Citations: 0
Abstract

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)

FAPESP's process: 19/12294-5 - Theoretical calculations of electronic spectra (UV-Vis, fluorescence and circular dichroism) of molecules of pharmacological and applied interest
Grantee:Nelson Henrique Morgon
Support Opportunities: Regular Research Grants
FAPESP's process: 13/08293-7 - CCES - Center for Computational Engineering and Sciences
Grantee:Munir Salomao Skaf
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC