Chemo- and regioselective synthesis of polysubstituted 2-aminothiophenes by the cyclization of<i>gem</i>-dibromo or<i>gem</i>-dichloroalkenes with β-keto tertiary thioamides
Xuxue Zhang, Chuan Liu, Yupian Deng, Song Cao
Abstract
A facile and practical method for the synthesis of 2,3,4-trisubstituted 2-aminothiophenes by the cyclization of gem-dibromoalkenes or gem-dichloroalkenes with β-keto tertiary thioamides has been developed. The cyclization reaction proceeded chemoselectively and regioselectively under metal-catalyst-free conditions, providing various structurally diverse 2,3,4-trisubstituted N,N'-dialkyl 2-aminothiophenes in good to excellent yields.
Topics & Concepts
ChemistryRegioselectivityCombinatorial chemistryMedicinal chemistryOrganic chemistryStereochemistryCatalysisSynthesis of heterocyclic compoundsSynthesis and Reactivity of Sulfur-Containing CompoundsSynthesis and Reactivity of Heterocycles