85992-25-2Relevant articles and documents
Construction of 2,3-disubstituted benzo[: B] thieno[2,3- d] thiophenes and benzo[4,5]selenopheno[3,2- b] thiophenes using the Fiesselmann thiophene synthesis
Demina, Nadezhda S.,Irgashev, Roman A.,Rusinov, Gennady L.
, p. 3164 - 3168 (2020/05/08)
A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann thiophene synthesis. To realize this strategy, the Friedel-Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]thiophene and benzo[4,5]selenopheno[3,2-b]thiophene are of interest for further elaboration of organic semiconductor materials.
Synthesis of heterocycles from the products of anionic arylation of unsaturated compounds. 7*. Products of haloarylation of acrylic acid and its esters in the synthesis of benzo[b]thiophene derivatives
Obushak,Matiichuk,Martyak
, p. 878 - 884 (2007/10/03)
3-Chloro-2-chlorocarbonylbenzo[b]thiophenes were obtained on oxidation of Meerwein reaction products, viz. 3-aryl-2-halopropionic acids and their esters, with thionyl chloride in the presence of N-benzyl-N-methylmorpholinium chloride. Disubstituted thioureas were synthesized by the reaction of these compounds with ammonium thiocyanate and aromatic amines, and were cyclized by interaction with iodoacetic acid with the formation of 4-thiazolidinone derivatives. The same cyclization in the presence of aromatic aldehydes leads to the formation of the corresponding 5-arylidene-substituted 4-thiazolidinones.
Synthesis of the Monomethyl Isomers of Naphthothienoquinoline
Kudo, Hirotaka,Castle, Raymond N.,Lee, Milton L.
, p. 1761 - 1764 (2007/10/02)
The synthesis of naphthothienoquinoline (11) and four monomethyl isomers is described.
