20924-64-5Relevant academic research and scientific papers
Electroreductive Intermolecular Coupling of Chromones with Benzophenones: Synthesis of 2-Diarylmethylchromones and Tetrasubstituted Furans
Kise, Naoki,Nagamine, Hiroaki,Sakurai, Toshihiko
, p. 3662 - 3676 (2019)
The electroreductive coupling of chromones with benzophenones in the presence of TMSCl gave adducts reacted at the 2-position of chromones as trimethylsilyl ethers. From 3-methyl- and 3-phenylchromones, 2,3-cis-adducts were formed predominantly. The cis-adducts were isomerized to trans-ones by treatment with DBU. The detrimethylsilylation of the adducts with 1 M HCl aq/dioxane produced the corresponding alcohols. The dehydrosiloxylation of the adducts or dehydration of the desilylated alcohols brought about 2-diarylmethylchromones. The detrimethylsilylation of the adducts with TBAF and subsequent treatment with NaH afforded ring-opening products. The dehydration of the ring-opening products obtained from 3-methyl- and 3-phenylchromons brought about tetrasubstituted furans or dihydrobenzofuran-3-ones. The dehydrogenation of the adducts with DDQ and subsequent desilylation with 1 M HCl aq/dioxane gave 2-(diarylhydroxymethyl)chromones.
