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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
Author(s) -
Tréguier Bret,
Rasolofonjatovo Evelia,
Hamze Abdallah,
Provot Olivier,
WdzieczakBakala Joanna,
Dubois Joëlle,
Brion JeanDaniel,
Alami Mouad
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100540
Subject(s) - sonogashira coupling , chemistry , tandem , enyne , combinatorial chemistry , coupling (piping) , palladium , organic chemistry , catalysis , materials science , composite material , metallurgy
Abstract 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 iso CA‐4.