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Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles Using BF3⦁SMe2
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preparative Medicinal Chemistry. (Preparative medicinal chemistry)
2019 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 31-32, p. 5402-5408Article in journal (Refereed) Published
Abstract [en]

Herein, a general, solvent-free and straightforward thiomethylation of electron deficient heterocycles using BF3⦁SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3⦁SMe2

towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non-malodorous reagent while the discovery of novel chemical transformations using BF3⦁SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2019. no 31-32, p. 5402-5408
Keywords [en]
heterocycles, thiomethylation, reduction, nucleophilic substitution
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-383868DOI: 10.1002/ejoc.201900503ISI: 000483709700044OAI: oai:DiVA.org:uu-383868DiVA, id: diva2:1317846
Funder
Swedish Research Council, 2018-05133Available from: 2019-05-24 Created: 2019-05-24 Last updated: 2019-10-23Bibliographically approved

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