One-pot synthesis of functionalized benzo[b]thiophenes and their hetero-fused analogues via intramolecular copper-catalyzed S-arylation of in situ generated enethiolates
| Autor: | Hiriyakkanavar Ila, B. Saraiah, S. Vijay Kumar, Anand Acharya |
|---|---|
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
In situ Phenyl isothiocyanate Aryl Organic Chemistry One-pot synthesis Stereoisomerism Thiophenes Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Heterocyclic Compounds Intramolecular force Organic chemistry Sulfhydryl Compounds Organic Chemicals Acetonitrile Dithiocarbamate Alkyl Copper |
| Zdroj: | The Journal of organic chemistry. 80(5) |
| ISSN: | 1520-6904 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|