109480-69-5Relevant articles and documents
Novel one-pot synthesis of polysubstituted isocoumarins from arynes and trifluoroacetylated β-diketones
Okuma, Kentaro,Hirano, Koki,Tanabe, Yukiko,Itoyama, Ryoichi,Miura, Atsumi,Nagahora, Noriyoshi,Shioji, Kosei
, p. 492 - 494 (2014)
Polysubstituted isocoumarins such as thunberginol A were synthesized by the reaction of substituted 2-(trimethylsilyl)-phenyl triflate with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded via carboncarbon bond insertion of aryne followed by intramolecular cyclization and CF3 anion extrusion. The C(..O)CF3 unit has high potential for not only the nucleophilic moiety but also a useful leaving group of CF3.
Reaction of arynes with trifluoroacetylated β-diketones: Novel formation of isocoumarins and phenanthrenes
Okuma, Kentaro,Tanabe, Yukiko,Fukami, Takuto,Ishibashi, Yuto
, (2018/11/10)
Polysubstituted isocoumarins were synthesized by the reaction of substituted 2-(trimethylsilyl)aryl triflates with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded through carbon-carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β-diketones to afford phenanthrenes and 1,2-diarylethanones. Although reaction of 2-(trimethylsilyl)phenyl triflate with 1,1,1-trifluoro-4′-methylbenzoylacetone in the presence of CsF gave 3-(4′-methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9-(4-methylbenzoyl)-10-trifluoromethylphenanthrene in 35% yield.
Synthesis of 3-arylisocoumarins, including thunberginols A and B, unsymmetrical 3,4-disubstituted isocoumarins, and 3-ylidenephthalides via iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids
Rossi, Renzo,Carpita, Adriano,Bellina, Fabio,Stabile, Paolo,Mannina, Luisa
, p. 2067 - 2081 (2007/10/03)
3-Aryl-4-iodoisocoumarins, which were readily and efficiently prepared by regioselective iodolactonization of methyl 2-ynylbenzoates or the corresponding carboxylic acids, were used as precursors either to 3-arylisocoumarins, including naturally-occurring