David Emilie, Perrin Julie, Pellet-Rostaing Stéphane, Fournier dit Chabert Jérémie, Lemaire Marc
Université Claude Bernard Lyon 1, Laboratoire de Catalyse et Synthèse Organique, CPE bât 308, UMR 5181, 43 Bd du 11 novembre 1918, 69622 Villeurbanne Cedex, France.
J Org Chem. 2005 Apr 29;70(9):3569-73. doi: 10.1021/jo0500378.
[reaction: see text] Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-arylbenzo[b]thiophenes with heteroatoms at the 3-positions directly from the benzo[b]thiophene core by using an aromatic nucleophilic substitution reaction and Heck-type coupling. This methodology provides 2-aryl-3-amino or phenoxybenzo[b]thiophenes in about 35% overall yield in 5 steps.
[反应：见正文] 苯并[b]噻吩衍生物之所以重要，部分原因在于它们用作选择性雌激素受体调节剂。它们通常通过分子内环化合成。在此，我们提出了一种直接从苯并[b]噻吩核心出发，利用芳香亲核取代反应和Heck型偶联反应合成3位带有杂原子的2-芳基苯并[b]噻吩的方法。该方法通过5步反应以约35%的总收率提供2-芳基-3-氨基或苯氧基苯并[b]噻吩。
