109480-69-5Relevant academic research and scientific papers
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.
Ruthenium(II)-Catalyzed Construction of Isocoumarins via Dual C-H/C-C Activation of Sulfoxonium Ylides
Wen, Si,Chen, Yanhui,Zhao, Zemin,Ba, Dan,Lv, Weiwei,Cheng, Guolin
, p. 1216 - 1223 (2020/01/09)
A ruthenium(II)-catalyzed annulation between two molecules of sulfoxonium ylides is achieved, generating a variety of substituted isocoumarins in reasonable yields. This strategy features dual C-H/C-C activation in one pot and has a wide substrate scope and good functional group tolerance.
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.
Super acid catalysed sequential hydrolysis/cycloisomerization of o-(acetylenic)benzamides under microwave condition: Synthesis, antinociceptive and antiinflammatory activity of substituted isocoumarins
Praveen, Chandrasekaran,Dheenkumar,Perumal
, p. 71 - 83 (2013/05/09)
Synthesis of isocoumarins and related compounds via triflic acid promoted hydrolysis/cyclization sequence of 2-(alkynyl)benzamides under microwave condition was achieved. The substrate scope of the reaction was broad to include not only aromatic but also
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
A Convenient Synthesis of 3-Substituted 8-Methoxy- and 6,8-Dimethoxyisocoumarins
Lewis, Christopher N.,Spargo, Peter L.,Staunton, James
, p. 944 - 946 (2007/10/02)
The reaction of N-methoxy-N-methylamides with the anion of ethyl 2-methoxy-, or 2,4-dimethoxy-6-methylbenzoate gives the corresponding ketones, which are cyclised to give the 3-substituted 8-methoxy- and 6,8-dimethoxyisocoumarins in good overall yield.
