title: One-pot synthesis of functionalized benzo[b]thiophenes and their hetero-fused analogues via intramolecular copper-catalyzed S-arylation of in situ generated enethiolates.
abstract: An efficient one-pot synthesis of highly functionalized multisubstituted benzo[b]thiophenes and their hetero-fused analogues, such as thieno[2,3-b]thiophenes, indolo[2,3-b]thiophenes, and pyrazolo[3,2-c]thiophenes, has been reported. The overall strategy involves sequential base-mediated condensation of 2-bromohet(aryl)acetonitrile precursors with (het)aryl/alkyl dithioesters or other thiocarbonyl species such as dimethyl trithiocarbonate, S-methyl xanthates, methyl N-imidazolyl dithioate, N-alkyl dithiocarbamate, and phenyl isothiocyanate, followed by intramolecular copper-catalyzed arylthiolation of in situ generated enethiolates, furnishing a broad range of 2-functionalized 3-cyanobenzo[b]- and/hetero-fused thiophenes in high yields.
authors: New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research , Jakkur, Bangalore 560064, India.
authors: Anand
authors: A
authors: Acharya
authors: S
authors: S
authors: Vijay Kumar
authors: B
authors: B
authors: Saraiah
authors: H
authors: H
authors: Ila
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009930:Organic Chemicals; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; D009930:Organic Chemicals; D013438:Sulfhydryl Compounds; D013876:Thiophenes; D003300:Copper