56973-60-5Relevant academic research and scientific papers
Facile palladium-catalyzed synthesis of 3-oxo-1,3-dihydro-1- isobenzofuranyl alkanoates from 2-bromobenzaldehyde and carboxylic acids
Cho, Chan Sik,Baek, Dong Yeol,Kim, Hye-Young,Shim, Sang Chul,Oh, Dae Hee
, p. 1139 - 1145 (2000)
2-Bromobenzaldehyde reacts with carboxylic acids in acetonitrile under carbon monoxide pressure in the presence of a catalytic amount of a palladium catalyst to give the corresponding 3-oxo-1,3-dihydro-1-isobenzofuranyl alkanoates in high yields.
Anhydrides of Arylfuran and Arylpyran Pseudoacids: Formation and Structures; C–O Bond Lengths Trends in Pseudo o-Formylbenzoic Acid Derivatives
O’Loughlin, Emily,Valente, Edward J.
, p. 193 - 205 (2019)
Abstract: Three methods for producing anhydrides of arylfuran and arylpyran pseudoacids were explored. These included thermal dehydration, phosgene or thionly chloride activation and decomposition, and dicyclohexylcarbodiimide activation and coupling. Derivatives of the cyclic forms of o-formylbenzoic acid, o-acetylbenzoic acid, 2-carboxyphenylacetaldehyde and of 4,4-dimethyl-3,4-dihydro-3-hydroxy-[1H]-isobenzopyran-1-one were formed including dipseudoanhydides and normal-pseudo anhydrides. Crystal and molecular structures for meso and (R,R/S,S)-bis(1[3H]-isobenzofuranone-3-yl)ether, (R,R/S,S)-bis(3-methyl-1[3H]-isobenzofuranone-3yl)ether, meso (3,4-dihydro-[1H]-isobenzopyran-1-one-3-yl)ether, 3-benzoyloxy-1[3H]-isobenzofuranone, 3-benzoyloxy-3-methyl-1[3H]isobenzofuranone, 3-(4′-nitrobenzoyloxy)-4,4-dimethyl-3,4-dihydro-[1H]-isobenzopyran-1-one, and (1[3H]-isobenzofuranone-3-yl)(4,4,dimethyl-3,4-dihydro-[1H]-isobenzopyran-1-one-3-yl)ether are reported. Endocyclic pseudoacyl C–O bonds are always longer than the exocyclic pseudoacyl C–O bonds. It is possible to refine the previously established C–O bond length dependencies on the pKa (of the conjugate acids) of the leaving groups for 3-substituted 1-[3H]-isobenzofuranones. Of six dipseudoanhydrides studied, conformations are found with exocyclic C–O(ether) linkages synclinal to the endocyclic C–O and away from the ring (exo conformation) in two meso structures, two of three RR/SS forms and in a chiral unsymmetrical form. An endo conformation is observed in one of the RR/SS forms. In three normal-pseudo anhydrides, both endo and exo conformations are observed. Graphic Abstract: Synthetic methods for formation of anhydrides of several arylfuran and arylpyran pseudoacids are described, and the pseudoacyl C–O bond length trends are determined for leaving groups spanning over 30 pKa units.[Figure not available: see fulltext.]
Palladium-catalyzed synthesis of 3-oxo-1,3-dihydro-1-isobenzofuranyl alkanoates from 2-bromobenzaldehyde and sodium alkanoates
Cho, Chan Sik,Baek, Dong Yeol,Shim, Sang Chul
, p. 289 - 291 (1999)
2-Bromobenzaldehyde reacts with sodium alkanoates in acetonitrile under carbon monoxide pressure in the presence of a catalytic amount of bis(triphenylphosphine)palladium(II) chloride to afford the corresponding 3- oxo-1,3-dihydro-1-isobenzofuranyl alkano
Synthesis of Enantioenriched Phthalide and Isoindolinone Derivatives from 2-Formylbenzoic Acid
Niedek, Dominik,Schuler, S?ren M.M.,Eschmann, Christian,Wende, Raffael C.,Seitz, Alexander,Keul, Felix,Schreiner, Peter R.
, p. 371 - 382 (2016/12/24)
Transformations of 2-formylbenzoic acid provide direct access to a series of heterocyclic organic compounds such as phthalides and isoindolinones. Here, we use (+)-cinchonine as a catalyst in conjunction with nonafluoro-tert-butanol as a hydrogen-bond donor to afford enantiomerically enriched acylated 3-hydroxyphthalides with up to 99% yield and 90% ee through dynamic kinetic resolution. Moreover, various 3-alkoxyphthalides as well as 2-alkyl-3-hydroxy-1-isoindolinones were synthesized from 2-formylbenzoic acid.
