The synthesis of 4-arylphenalenones revisited

[Display omitted] The synthesis of 4-phenylphenalenones, a group of phytoalexins exclusive from Musa acuminata (bananas), has been revisited to extend the scope of the derivatives that can be prepared. The discovery that 4-methoxyphenalenone participates in a selective substitution reaction allowed...

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Bibliographic Details
Published inResults in Chemistry Vol. 4; p. 100348
Main Authors Hoyos, Catalina, Cano, Marisol, Barrera, Julián, Otálvaro, Felipe
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.01.2022
Elsevier
Subjects
Nucleophilic aromatic substitution
Phenylphenalenones
Sandmeyer reaction
Suzuki cross-coupling
Nucleophilic aromatic substitution
Sandmeyer reaction
Phenylphenalenones
Suzuki cross-coupling
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Summary:[Display omitted] The synthesis of 4-phenylphenalenones, a group of phytoalexins exclusive from Musa acuminata (bananas), has been revisited to extend the scope of the derivatives that can be prepared. The discovery that 4-methoxyphenalenone participates in a selective substitution reaction allowed the preparation of 4-bromophenalenone, which proved to be an efficient substrate for Suzuki cross-couplings. The results solve the previously uncovered problem of preparing electron-rich 4-heteroarylphenalenones and provide a general synthesis of this type of phytoalexins.
ISSN:2211-7156
2211-7156
DOI:10.1016/j.rechem.2022.100348