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Synthesis of new methylated thieno[2,3-a] and [3,2-b]carbazoles by reductive cyclization of 6-(2′-Nitrophenyl)benzo[b]thiophenes obtained by palladium-catalyzed cross-coupling isabel

Ferreira, C. F. R. ; Queiroz, Maria-João R. P. ; Kirsch, Gilbert

Journal of heterocyclic chemistry, 2001-05, Vol.38 (3), p.749-754 [Periódico revisado por pares]

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Synthesis of new methylated thieno[2,3-a] and [3,2-b]carbazoles by reductive cyclization of 6-(2′-Nitrophenyl)benzo[b]thiophenes obtained by palladium-catalyzed cross-coupling isabel
Autor: Ferreira, C. F. R. ; Queiroz, Maria-João R. P. ; Kirsch, Gilbert
É parte de: Journal of heterocyclic chemistry, 2001-05, Vol.38 (3), p.749-754
Notas: ark:/67375/WNG-4ZK19DM9-T
istex:4626129F0AFA293092ABF9091B3BB2AE4CF64B93
ArticleID:JHET5570380334
Descrição: The synthesis of new methylated thieno[2,3‐a] and [3,2‐b]carbazoles (5) (R=H) was achieved by a palladium‐catalyzed cross‐coupling, intramolecular reductive cyclization sequence of reactions. The cyclization precursors 6‐(2′‐nitrophenyl)benzo[b]thiophenes (3) were obtained by Suzuki cross‐coupling of 6‐boronated methylbenzo[b]thiophenes intermediates (2) with 2‐bromo or iodonitrobenzene. The boronated intermediates (2) were prepared via bromine‐lithium exchange followed by boron transmetalation and coupled in situ using Pd(OAc)2 giving thus a “one‐pot” three steps reaction from the 6‐bromobenzo[b]thio‐phenes (1) to the cyclization precursors (3). In the reductive cyclization step, N‐ethylthienocarbazoles (5) (R=Et) were also obtained. Several experiments have been made varying the amount of triethylphosphite and the time of reaction, to avoid their formation.
Editor: Hoboken: Wiley-Blackwell
Idioma: Inglês

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