|
|
|
|
|
| Queiroz, Maria João R.P.; Begouin, Agathe; Ferreira, Isabel C.F.R.; Kirsch, Gilbert; Calhelha, Ricardo C.; Barbosa, Sandra; Estevinho, Leticia M.. |
| Several diarylamines in the benzo[b]thiophene series were prepared in good to high yields by palladium-catalysed amination of ethyl 3-bromobenzo[b]thiophene-2-carboxylate with anilines and 5-aminoindole in the presence of Pd(OAc)2, BINAP and Cs2CO3 in toluene. The presence of the ester group at the 2-position of the benzo[b]thiophene moiety increases the yields and lowers the heating times relative to the reactions performed with 3-bromobenzo[b]thiophene. When aminopyridines were used instead of anilines, the ligand and the solvent need to be changed to XANTHPHOS and dioxane in the amination reaction. With 2-aminopyridine a onepot C−N coupling and intramolecular cyclization involving the nitrogen atom of the pyridine ring occurred, with loss of ethanol,... |
| Tipo: Article |
Palavras-chave: Amination; Antimicrobial activity; Benzothiophenes; Diarylamines; Fluorescence; Palladium. |
| Ano: 2004 |
URL: http://hdl.handle.net/10198/820 |
| |
|
| |
|
|
| Ferreira, Isabel C.F.R.; Queiroz, Maria João R.P.; Kirsch, Gilbert. |
| Diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups, were prepared by Buchwald– Hartwig C–N coupling in moderate to high yields. The conditions used were Pd(OAc)2 (3 mol%), BINAP as ligand (4 mol%) and Cs2CO3 as base (1.4 equiv.), in toluene at 1008C, being 6-bromo or amino benzo[b]thiophenes coupled, respectively, with substituted anilines or phenylbromides. The 6-aminobenzo[b]thiophene derivatives were also prepared by palladium catalyzed C–N coupling of the corresponding 6-bromo compounds with benzophenone imine, followed by acidic hydrolysis of the imino derivatives. When 4-nitrobromobenzene and 4-bromobenzonitrile were used as coupling components, triarylamines were also isolated in small amounts. The presence... |
| Tipo: Article |
Palavras-chave: Buchwald–Hartwig coupling; Palladium; Amination; Diarylamines; Benzo[b]thiophenes. |
| Ano: 2003 |
URL: http://hdl.handle.net/10198/818 |
| |
|
|
|
