Regioselective N-Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate-Catalyzed Substitution of Alcohols and Alkyl Group Migrations

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MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversity of Calcutta-
Autor(es): dc.contributorCSIR-Central Drug Research Institute-
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.contributorP.O. Box 1982-
Autor(es): dc.contributorUniversidade Estadual de Campinas (UNICAMP)-
Autor(es): dc.creatorDuari, Surajit-
Autor(es): dc.creatorBiswas, Subrata-
Autor(es): dc.creatorRoy, Arnab-
Autor(es): dc.creatorMaity, Srabani-
Autor(es): dc.creatorMishra, Abhishek Kumar-
Autor(es): dc.creatorde Souza, Aguinaldo R.-
Autor(es): dc.creatorElsharif, Asma M.-
Autor(es): dc.creatorMorgon, Nelson H.-
Autor(es): dc.creatorBiswas, Srijit-
Data de aceite: dc.date.accessioned2025-08-21T17:01:05Z-
Data de disponibilização: dc.date.available2025-08-21T17:01:05Z-
Data de envio: dc.date.issued2022-04-29-
Data de envio: dc.date.issued2022-04-29-
Data de envio: dc.date.issued2022-02-14-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1002/adsc.202101196-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/231595-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/231595-
Descrição: dc.descriptionA 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.).-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionDepartment of Chemistry University of Calcutta, 92, A. P. C. Road, West Bengal-
Descrição: dc.descriptionDepartment of Medicinal and Process Chemistry CSIR-Central Drug Research Institute, U. P.-
Descrição: dc.descriptionDepartment of Chemistry School of Science São Paulo State University, São Paulo-
Descrição: dc.descriptionDepartment of Chemistry Imam Abdulrahman Bin Faisal University P.O. Box 1982-
Descrição: dc.descriptionDepartment of Physical Chemistry Institute of Chemistry Campinas State University, São Paulo-
Descrição: dc.descriptionDepartment of Chemistry School of Science São Paulo State University, São Paulo-
Descrição: dc.descriptionCNPq: 303581/2018-2-
Descrição: dc.descriptionCNPq: 305541/2017-0-
Formato: dc.format865-872-
Idioma: dc.languageen-
Relação: dc.relationAdvanced Synthesis and Catalysis-
???dc.source???: dc.sourceScopus-
Palavras-chave: dc.subjectAlcohols-
Palavras-chave: dc.subjectAlkylation-
Palavras-chave: dc.subjectHeterocycles-
Palavras-chave: dc.subjectMeOTf Catalyst-
Palavras-chave: dc.subjectNucleophilic Substitution-
Palavras-chave: dc.subjectRearrangement-
Título: dc.titleRegioselective N-Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate-Catalyzed Substitution of Alcohols and Alkyl Group Migrations-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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