29539-21-7Relevant academic research and scientific papers
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 isocoumarin derivatives via the copper-catalyzed tandem sequential cyclization of 2- halo-N-phenyl benzamides and acyclic 1,3-diketones
Kavala, Veerababurao,Wang, Cheng-Chuan,Barange, Deepak Kumar,Kuo, Chun-Wei,Lei, Po-Min,Yao, Ching-Fa
experimental part, p. 5022 - 5029 (2012/07/16)
A facile and rapid synthesis of isocoumarin derivatives using a copper-catalyzed tandem C-C/C-O coupling strategy from readily available substrates is described. The reactions of a wide range of 2-iodo-N-phenyl benzamides and acyclic diketones as starting materials were investigated.
Ortho-Induced transition-metal-free C-arylation cyclization reaction for the synthesis of polysubstituted isocoumarins
Liu, Lei,Hu, Jie,Wang, Xiang-Chuan,Zhong, Mei-Jin,Liu, Xue-Yuan,Yang, Shang-Dong,Liang, Yong-Min
supporting information; experimental part, p. 5391 - 5395 (2012/09/08)
A new protocol for the synthesis of polysubstituted isocoumarins from 2-iodobenzoic acid and β-diketone compounds has been developed. The occurrence of C-arylation cyclization reaction in transition-metal-free systems and ortho-induced substrates has been exploited. Reactions using these inexpensive conditions have displayed high functional group tolerance and excellent yields.
Assembly of 3-substituted isocoumarins via a CuI-catalyzed domino coupling/addition/deacylation process
Cai, Shangjun,Wang, Fei,Xi, Chanjuan
experimental part, p. 2331 - 2336 (2012/05/05)
An efficient strategy for the synthesis of a variety of 3-substituted isocoumarins has been developed. The reaction proceeded from o-halobenzoic acids and 1,3-diketones via a copper(I)-catalyzed domino reaction in DMF under the action of K3PO4 at 90-120 °C without a ligand to afford the corresponding 3-substituted isocoumarin derivatives in good to excellent yields. o-Halobenzoic acids could be o-iodobenzoic acid, o-bromobenzoic acid, and o-chlorobenzoic acid derivatives. 1,3-Diketones could be alkyl- and aryl-substituted 1,3-diketones.
Iridium-catalyzed oxidative lactonization and intramolecular Tishchenko reaction of δ-ketoaldehydes for the synthesis of isocoumarins and 3,4-dihydroisocoumarins
Suzuki, Takeyuki,Yamada, Taichiro,Watanabe, Kazuhiro,Katoh, Tadashi
, p. 2583 - 2585 (2007/10/03)
Two new cyclizations of ketoaldehydes have been developed using an Ir-ligand bifunctional catalyst. Oxidative lactonization of δ- ketoaldehydes proceeded smoothly at room temperature to give coumarin derivatives in excellent yields. Intramolecular Tishche
Synthesis of isocoumarins and α-pyrones via tandem Stille reaction/heterocyclization
Cherry, Khalil,Parrain, Jean-Luc,Thibonnet, Jerome,Buchene, Alain,Abarbri, Mohamed
, p. 6669 - 6675 (2007/10/03)
A general route to α-pyrones and 3-substituted isocoumarins from (Z)-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-β-iodovinylic acids 1a-f or 2-iodobenzoic acids 4a-c with various allenyl-tributyltin reagents in the presence of palladium acetate, triphenylphosphine, and tetrabutylammonium bromide in dimethylformamide provided good yields of the corresponding α-pyrones 3a-k or 3-substituted isocoumarins 5a-g via tandem Stille reaction and 6-endo-dig oxacyclization.
Nickel-catalyzed direct electrochemical cross-coupling between aryl halides and activated alkyl halides
Durandetti, Muriel,Nedelec, Jean-Yves,Perichon, Jacques
, p. 1748 - 1755 (2007/10/03)
The electrochemical reduction of a mixture of aryl halides and activated alkyl halides in DMF in the presence of catalytic amount of NiBr2bipy leads to cross-coupling products in good to high yields. The method applies to the synthesis of α-aryl ketones, α-aryl esters, and allylated compounds from readily available organic halides. Optimization of the process has been obtained by slowly adding the most reactive organic halide (usually the activated alkyl halide) during the electrolysis which is best conducted at 70 °C when aryl bromides are involved.
A novel method of arylation of α-chloroketones
Durandetti,Sibille,Nedelec,Perichon
, p. 145 - 151 (2007/10/02)
α-Arylated ketones were obtained in moderate to good yields by one-step electroreductive coupling of α-chloroketones and arylhalides in DMF and in the presence of a Al- or Zn-sacrificial anode and a catalytic amount of a nickel complex.
3-SUBSTITUTED ISOCOUMARINS FROM PHTHALIDE-3-PHOSPHONATES. A NOVEL SYNTHESIS
Napolitano, Elio,Ramacciotti, Antonella
, p. 443 - 444 (2007/10/02)
The title transformation was carried out in two steps by C(3) acylation of the phosphonate reagent followed by reduction with zinc in acetic acid.
