1192159-76-4Relevant academic research and scientific papers
Synthesis of divergent benzo[b]fluorenones through cycloaromatization reactions of 1,5-enynols and 1,5-diynols
Yan, Bingyu,Fu, Yang,Zhu, Hui,Chen, Zhiyuan
, p. 4246 - 4262 (2019)
A facile and efficient synthesis of divergent benzo[b]fluorenones is described through the use of dichlorobenzoquinone-promoted oxidative cycloaromatization reactions of acyclic 1,5-enynols and 1,5-diynols. The success of these cascade reactions depends on the chemoselectivity of the initial Meyer-Schuster rearrangement to produce allenol intermediate, which is followed by regioselective Schmittel cyclization and the subsequent Friedal-Crafts alkylation or radical attack at the terminal Ar moiety. Only an oxidant and a solvent were required in the reaction, thus delivering a small library of the expected polycarbocyclic products with excellent functional group tolerance under metal-free conditions. The absorption and photoluminescence properties of the selected benzo[b] fluorenones were also investigated. The results indicated that the compound (2h) which contained an electron-donating 4-OMe group at the phenyl moiety displayed deep green color emission (491 nm).
DDQ-Mediated Oxidative Radical Cycloisomerization of 1,5-Diynols: Regioselective Synthesis of Benzo[b]fluorenones under Metal-Free Conditions
Zhu, Hui,Chen, Zhiyuan
supporting information, p. 488 - 491 (2016/02/18)
A regio- and chemoselective oxidative cycloisomerization reaction of acyclic 1,5-diynols has been developed. The reaction proceeds under metal-free reaction conditions with high efficiency and broad functional group tolerance, which offers a general and straightforward access to benzo[b]fluorenones under metal-free conditions. The preliminary mechanistic studies revealed the possible involvement of a Meyer-Schuster rearrangement combined with an oxidative radical cyclization.
