Synthesis of <scp>3‐Methylthio</scp>‐benzo[<i>b</i>]furans/Thiophenes <i>via</i> Intramolecular Cyclization of <scp>2‐Alkynylanisoles</scp>/Sulfides Mediated by <scp>DMSO</scp>/<scp>DMSO</scp>‐<i>d</i><sub>6</sub> and <scp>SOCl<sub>2</sub></scp>
Beibei Zhang, Xiaoxian Li, Xuemin Li, Fengxia Sun, Yunfei Du
Abstract
Abstract Main observation and conclusion The reaction of 2‐alkynylanisoles/sulfides with SOCl 2 and DMSO was conducted to conveniently furnish the biologically interesting 3‐(methylthio)‐benzo[ b ]furans/thiophenes via intramolecular cyclization. DMSO acts as a solvent as well as a sulfur source and can also be replaced with DMSO‐ d 6 , enabling the incorporation of the SCD 3 moiety of DMSO‐ d 6 to the 3‐position of the heterocyclic frameworks.
Topics & Concepts
ChemistryMoietyIntramolecular forceSolventMedicinal chemistryStereochemistrySulfurOrganic chemistrySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods