Construction of 2-Arylbenzo[4,5]thieno[2,3-<i>d</i>]thiazole Skeleton via CuCl/S-Mediated Three-Component Reaction
Wei Zhang, Shanqing Tao, Huaibin Ge, Qiao Li, Zhenkang Ai, Xiaoxian Li, Beibei Zhang, Fengxia Sun, Xiaqing Xu, Yunfei Du
Abstract
An exclusive thiophene-fused polycyclic π-conjugated 2-arylbenzo[4,5]thieno[2,3-d]thiazole skeleton was constructed via a one-pot CuCl-mediated three-component reaction, using 2-(2-bromophenyl)acetonitrile and aromatic aldehydes as substrates and elemental sulfur as sulfur source in the presence of K2CO3 and 1,10-phen in DMSO. A plausible reaction mechanism was proposed, which involved formation of benzo[b]thiophen-2-amines through cyclization of 2-bromophenyl acetonitrile and sulfur, and subsequent intramolecular condensation/dehydrogenation with aromatic aldehydes.
Topics & Concepts
ChemistryThiazoleAcetonitrileIntramolecular forceSulfurDehydrogenationThiopheneConjugated systemComponent (thermodynamics)Medicinal chemistryCondensationOrganic chemistryCatalysisPolymerThermodynamicsPhysicsSulfur-Based Synthesis TechniquesSynthesis of heterocyclic compoundsMulticomponent Synthesis of Heterocycles