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Catalytic O- to N-Alkyl Migratory Rearrangement: Transition Metal-Free Direct and Tandem Routes to N-Alkylated Pyridones and Benzothiazolones
Ctr Biomed Res CBMR, Div Mol Synth & Drug Discovery, SGPGIMS Campus, Lucknow 226014, Uttar Pradesh, India.
Univ Estadual Campinas, UNICAMP, Inst Chem, Dept Phys Chem, BR-13083970 Campinas, SP, Brazil.
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Molecular Biology.ORCID iD: 0000-0002-7124-792X
Sao Paulo State Univ, UNESP, Sch Sci, BR-17033360 Bauru, SP, Brazil.
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2018 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 360, no 20, p. 3930-3939Article in journal (Refereed) Published
Abstract [en]

The present study reports the synthesis of N-alkylated pyridones and benzothiazolones via O- to N-alkyl group migration under transition metal-free TfOH-catalyzed reaction conditions for the first time, to the best of our knowledge. Primary as well as secondary alkyl groups smoothly migrate under the present reaction conditions. Moreover, a minor modification of the protocol used in this study is found to be applicable for an entirely new tandem synthesis of 2-alkoxy-N-heterocycles from the simplest starting materials in a solvent-free reaction conditions. Density Functional Theory (DFT) calculation identifies the energy species associated with the rearrangement, whereas, mechanistic experiments explore the role of the catalyst as the alkyl group transfer mediator.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2018. Vol. 360, no 20, p. 3930-3939
Keywords [en]
Benzothiazolones, Metal-free, Pyridones, Rearrangement, Tandem, DFT
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-369093DOI: 10.1002/adsc.201800664ISI: 000447633800012OAI: oai:DiVA.org:uu-369093DiVA, id: diva2:1289482
Available from: 2019-02-18 Created: 2019-02-18 Last updated: 2019-02-18Bibliographically approved

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Sanyal, Suparna

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