Regioselective Suzuki coupling of benzofuran or benzothiophene boronic acids and dibromo substituted naphthalenes: synthesis of a potent inhibitor of plasminogen activator inhibitor-1

Practical synthesis of polysubstituted naphthalene derivatives via HNTf2-catalyzed benzannulation reaction

“…Accordingly, the 4-chloro-, 4-bromo-and 4-methyl-substituted alkynes 4d-f were submitted to reaction and gave access to desired products 5d-f with comparable satisfactory results ( Table 3, entries 4-6). In the case of alkynes 4g and 4h, which are bearing electronwithdrawing/donating 4-trifluoromethyl and 4-methoxy groups, a reduced reaction efficiency could however be noticed (Table 3, entries [7][8]. Notably, the reaction of the electron rich alkyne 4h was faster and the aldehyde 1a was converted to 5h in 44% yield along with some unidentified by-products (Table 3, entry 8).…”

“…[1][2][3][4][5][6][7][8][9] Additionally, this particular aromatic structure can be found in numerous optical and electronic materials [10][11][12] and constitutes the backbone of many chiral ligands. 13 Nafacillin, 14 suramin, 15,16 which play a vital role in the control of microbial infection, are typical examples of drugs that present a naphthalene moiety ( Figure 1).…”

Site-specific preparation of 4-substituted-6-fluoro(carboalkoxyl)benzo[b]furans and benzo[b]thiophenes via base-catalyzed cyclization of enyne derivatives

“…Pale oil; 1 Under N 2 , a mixture of PdCl 2 (PPh 3 ) 2 (40 mg, 0.05 mmol) and CuI (20 mg, 0.10 mmol) was added into a flask. Then 4 mL of CH 3 CN, a-bromoacrylate (1 mmol) and terminal alkyne (1.2 mmol) were added sequentially.…”

“…The organic phase was washed with water (10 mL), and then dried over Na 2 SO 4 . After the solvent was removed, the residue was subjected to column chromatography to give 0.35 g of a yellow oil; 1 …”

“…Benzo[b]furans and benzo[b]thiophenes represent many naturally occurring and designed molecules responsible for a diverse range of biological responses [1][2][3][4][5][6]. Recently, fluorinated benzofurans and benzothiophenes have also found application in liquid crystal displays [7].…”