DMTSF-mediated electrophilic cyclization for the synthesis of 3-thiomethyl-substituted benzo[ b ]furan derivatives.

Autor: McGurk DT; Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. tkesharwani@uwf.edu., Knighten LE; Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. tkesharwani@uwf.edu., Peña Bú MJ; Department of Biology, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. pmasih@uwf.edu., Christofferson FI; Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. tkesharwani@uwf.edu., Rich SD; Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. tkesharwani@uwf.edu., Masih PJ; Department of Biology, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. pmasih@uwf.edu., Kesharwani T; Department of Chemistry, University of West Florida, 11000 University Pkway, Pensacola, FL 32514, United States. tkesharwani@uwf.edu.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2024 Oct 18. Date of Electronic Publication: 2024 Oct 18.
DOI: 10.1039/d4ob00958d
Abstrakt: Benzofuran is an important backbone for molecules that make up several pharmaceuticals, herbicides/pesticides, and organo-electronics. An environmentally benign dimethyl(methylthio)sulfonium tetrafluoroborate salt was used as an electrophile to induce cyclization of o -alkynyl anisoles to form 2,3-disubstituted benzofurans. The cyclization is performed at ambient reaction conditions, only takes 12 hours to get excellent yields, and shows a high tolerance for various substituted alkynes. Also, a sulfurmethyl group obtained after the cyclization reactions allows for a cascade cyclization, and an alkyne is used in the reaction to create a thieno[3,2- b ]benzofuran core structure.
Databáze: MEDLINE