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Synthesis of 7‐Allylated Benzofuran Derivatives from o‐ Allyloxyethynylbenzene via Claisen Rearrangement and TBAF‐Catalyzed Annulation
Author(s) -
Watanabe Kohei,
Mino Takashi,
Masuda Chihiro,
Yoshida Yasushi,
Sakamoto Masami
Publication year - 2019
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.201801800
Subject(s) - benzofuran , annulation , chemistry , claisen rearrangement , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry
The 7‐allylated benzofuran derivatives were synthesized via a continuous reaction of Claisen rearrangement and annulation using o‐ allyloxyetynylbenzene as starting material. In addition, it was observed that annulation of o ‐alkynylphenol proceeded under mild conditions when carried out in the presence of a catalytic amount of TBAF. Furthermore, these continuous reactions could be achieved in a one‐pot reaction and afforded not only 7‐allylbenzofurans but also 7‐alkenylbenzofurans by controlling the reaction temperature and time of the annulation. Finally, we demonstrated that 7‐allylbenzofuran and 7‐alkenylbenzofuran could be converted into 7‐(2‐formylvinyl)benzofuran and 7‐formylbenzofuran derivatives, respectively. Therefore, various 7‐substituted benzofuran derivatives could be synthesized according to this synthetic strategy.