Details

Autor(en) / Beteiligte

• Tréguier, Bret
• Rasolofonjatovo, Evelia
• Hamze, Abdallah
• Provot, Olivier
• Wdzieczak-Bakala, Joanna
• Dubois, Joëlle
• Brion, Jean-Daniel
• Alami, Mouad

Titel

Synthesis of 2-(1-Phenylvinyl)benzofurans and 2-(1-Phenylvinyl)indoles as Antimitotic Agents by a Tandem Palladium-Assisted Coupling-Cyclization Reaction between 1-Phenylvinyl Iodides and ortho-Substituted Arylalkynes

Ist Teil von

• European Journal of Organic Chemistry, 2011-09, Vol.2011 (25), p.4868-4876

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2011

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A series of functionalized 2‐(1‐phenylvinyl)benzofurans 2 and 2‐(1‐phenylvinyl)indoles 3 were prepared from 1‐phenylvinyl iodides and silylated alkynes in a one‐pot reaction. After a desilylation step, the Sonogashira coupling reaction between the resulting terminal alkynes and 1‐phenylvinyliodide derivatives 6 gave enyne intermediates, which underwent a 5‐endo‐dig cyclization to afford 2‐(1‐phenylvinyl) heterocycles 2 and 3 in good yields. This method provides a rapid and efficient approach to build up benzoheterocycle‐based isocombretastatin A‐4 analogues of biological interest. From this series of compounds, the indoles 3o and 3r inhibited tubulin assembly at a micromolar level comparable to that of isoCA‐4. An efficient tandem Pd‐catalyzed reaction of 1‐phenylvinyl iodides with silylatedalkynes was developed for accessing functionalized 2‐(1‐phenylvinyl)benzofuran and ‐indole derivatives of biological interest in a single synthetic operation.