445475-94-5

Upstream product

• 24434-84-2 benzo[b]thiophene-3-carbonitrile 
• 696-62-8 para-iodoanisole 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 5874-09-9 methyl (4-methoxyphenyl)carbodithioate 
• 326-62-5 2-fluorophenyl acetonitrile 
• 19472-74-3 2-(2-bromophenyl)acetonitrile 
• 40400-15-5 2-(2-iodophenyl)acetonitrile 
• 104-92-7 1-bromo-4-methoxy-benzene 

Relevant academic research and scientific papers

Synthesis of Substituted Benzo[ b]thiophenes via Base-Promoted Domino Condensation-Intramolecular C-S Bond Formation

A novel synthesis of 2,3-substituted benzothiophenes is reported, involving a tandem base-mediated condensation of o-iodoarylacetonitriles/acetates/ketones with (hetero)aryldithioesters and an intramolecular C-S bond formation. The reaction affords divers

Diversity-Oriented Synthesis of Substituted Benzo[b]thiophenes and Their Hetero-Fused Analogues through Palladium-Catalyzed Oxidative C-H Functionalization/Intramolecular Arylthiolation

An efficient, high yielding route to multisubstituted benzo[b]thiophenes has been developed through palladium-catalyzed intramolecular oxidative C-H functionalization-arylthiolation of enethiolate salts of α-aryl-β-(het)aryl/alkyl-β-mercaptoacrylonitriles/acrylates or acrylophenones. The overall strategy involves a one-pot, two-step process in which enethiolate salts [generated in situ through base-mediated condensation of substituted arylacetonitriles, deoxybenzoins, or arylacetates with (het)aryl (or alkyl) dithioates] are subjected to intramolecular C-H functionalization-arylthiolation under the influence of a palladium acetate (or palladium chloride)/cupric acetate catalytic system and tetrabutylammonium bromide as additive in N,N-dimethylformamide (DMF) as solvent. In a few cases, the yields of benzo[b]thiophenes were better in a two-step process by employing the corresponding enethiols as substrates. In a few examples, Pd(OAc)2 (or PdCl2) catalyst in the presence of oxygen was found to be more efficient than cupric acetate as reoxidant, furnishing benzothiophenes in improved yields by avoiding formation of side products. The method is compatible with a diverse range of substituents on the aryl ring as well as on the 2- and 3-positions of the benzothiophene scaffold. The protocol could also be extended to the synthesis of a raloxifene precursor and a tubulin polymerization inhibitor in good yields. The versatility of this newly developed method was further demonstrated by elaborating it for the synthesis of substituted thieno-fused heterocycles such as thieno[2,3-b]thiophenes, thieno[2,3-b]indoles, thieno[3,2-c]pyrazole, and thieno[2,3-b]pyridines in high yields. A probable mechanism involving intramolecular electrophilic arylthiolation via either a Pd-S adduct or palladacycle intermediate has been proposed on the basis of experimental studies.

One-pot synthesis of 2,3-substituted benzo[b]thiophenes via Cu(i) catalysed intramolecular cyclisation from dithioesters

Efficient synthesis of benzo[b]thiophenes from o-halophenyl acetonitrile has been achieved. This novel one-pot procedure involves CuI and pivalic acid catalyzed C-S bond formation using dithioesters followed by a heterocyclization reaction. This efficient

Synthesis of benz[c]benzothiopheno[2,3-e]azepines via Heck-type coupling and Pictet-Spengler reaction

New benz[c]benzothiopheno[2,3-e]azepine derivatives 1 of potential biological properties were synthesised in four steps from bromobenzo[b] thiophene. The synthetic pathway is based on 'Heck-type' and Pictet-Spengler reactions. Georg Thieme Verlag Stuttgar

Synthesis of new 2-arylbenzo[b]thiophenes using 'Heck-type' technology

Direct 3-substituted benzothiophene arylation using a Heck-type reaction with Pd(OAc)2/n-Bu4NBr as a catalytic system is reported. This reaction was found to perform relatively fast whatever the electron-donating or the electron-withdrawing group at position 3. We also extended this reaction to several aromatic halides, such as benzene, naphthalene and pyridine derivatives, synthesising new 2-arylbenzo[b]thiophenes in moderate to good yields.