69322-20-9

Upstream product

• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 100-19-6 (4-nitrophenyl)ethanone 
• 119-67-5 o-carboxybenzaldehyde 
• 78812-73-4 C₁₀H₁₃NO₅ 
• 64611-67-2 2-hydroxy-1-(4-nitrophenyl)ethanone 
• 703-59-3 homophthalic anhydride 

Downstream Products

• 124033-50-7 4-nitro-N-<(3-oxo-1,3-dihydroisobenzofuran-1-yl)methyl>benzamide 
• 124033-29-0 N-(4-nitrophenyl)-2-(3-oxo-1,3-dihydroisobenzofuran-1-yl)acetamide 
• 69322-14-1 o-(4'-nitrobenzoylvinyl)benzoyl chloride 

Relevant academic research and scientific papers

Efficient PhB(OH)2-catalyzed one-pot synthesis of 3-substituted isoindolin-1-ones and isobenzofuran-1(3H)-ones under solvent free conditions

An efficient and practical one-pot synthesis of 3-substituted isoindolin-1-ones and isobenzofuran-1(3H)-ones has been developed under solvent free-conditions using non-toxic and cheap phenylboronic acid as excellent catalyst. This strategy involves the sequential two-step Mannich/lactamization cascade reaction of inexpensive 2-formylbenzoic acid with primary amines and a wide variety of ketones, and an aldol/lactonization cascade reaction of 2-formylbenzoic acid with a broad range of ketones.

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.

Synthesis, molecular properties prediction and cytotoxic screening of 3-(2-aryl-2-oxoethyl)isobenzofuran-1(3H)-ones

In the present investigation, a collection of nineteen 3-(2-aryl-2-oxoethyl)isobenzofuran-1(3H)-ones was synthesized and screened for their cytotoxic activity against a panel of three leukemia cancer cell lines. The compounds were prepared via ZrOCl2·8H2O catalyzed condensation reactions between phthalaldehydic acid and different acetophenones. The reactions were carried out free of solvent and the isobenzofuran-1(3H)-ones were obtained in good yields (80-92%). The identities of the synthesized compounds were confirmed upon IR and NMR (1H and 13C) spectroscopy as well as high resolution mass spectrometry analyses. Structures of compounds 1, 4 and 16 were also investigated by X-ray analysis. The synthesized compounds were submitted to in vitro bioassays against HL-60, K562 and NALM6 cancer cell lines using MTT cytotoxicity assay. After 48 h of treatment, twelve derivatives were able to reduce cell viability and presented IC50 values equal to or below 20 μmol L-1 against at least one of the evaluated lineages. The most active compound corresponded to 3-(3-methylphenyl-2-oxoethyl)isobenzofuran-1(3H)-one (18) (IC50 values obtained for HL-60, K562 and NALM6 were, respectively, 13.5 μmol L-1, 8.83 μmol L-1, and 5.24 μmol L-1). In addition, compound 18 was capable of triggering apoptosis on NALM6 cells. All isobenzofuranones herein evaluated did not present cytotoxicity on peripheral blood mononuclear cells (PBMC), suggesting selective cytotoxic effect on leukemic cells. A computational study allowed prediction of pharmacokinetics and drug-likeness properties of the synthesized compounds. DFT calculations were performed to obtain the energy values of HOMO, LUMO, and dipole moments of isobenzofuranones.

1-Methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles: An efficient and reusable catalyst for synthesis of mono- and bis-isobenzofuran-1(3H)-ones under solvent-free conditions

1-Methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles ([HSO3PMIM]OTf-SiO2@MNPs) was prepared by immobilization of [HSO3PMIM]OTf onto the surface of silica-coated Fe3O4 nanoparticles and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), and FT-IR techniques. Efficient synthesis of mono- and bis-isobenzofuran-1(3H)-ones was performed in the presence of this catalyst under thermal conditions and MW irradiation. The catalyst could be easily separated by an external magnet and reused six times under thermal conditions and MW irradiation without significant loss of its activity.

One-pot synthesis of isobenzofuran-1(3H)-ones using sulfuric acid immobilized on silica under solvent-free conditions and survey of third-order nonlinear optical properties

Solvent-free synthesis of isobenzofuran-1(3H)-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H2SO4-SiO2) in excellent yields (70-88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques.

One pot solvent free synthesis and in vitro antitubercular screening of 3-Aracylphthalides against Mycobacterium tuberculosis

One pot synthesis of 3-Aracylphthalide was accomplished in good yield by reacting 2-carboxy benzaldehyde with various aromatic methyl ketones in presence of methane sulphonic acid. Various phthalides thus obtained were characterized with spectral techniques. These phthalides were subjected to in vitro antitubercular screening against Mycobacterium tuberculosis H37Ra (MTB) by using XRMA protocol. Among the phthalides screened, four exhibited half maximal inhibitory concentration (IC50) in the range of 0.81-1.24 μg/ml thereby providing potential lead compounds for future drug discovery studies.

ZrOCl2·8H2O catalyzed solvent-free synthesis of isobenzofuran-1(3H)-ones

ZrOCl2·8H2O catalyzed environmentally benign synthesis of isobenzofuran-1(3H)-ones are described. ZrOCl2· 8H2O appeared to be an excellent catalyst for the condensation and reactions. Reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl and cyclic ketones was initiated by condensation and occurred in one step providing excellent yields (90-98%).

Synthesis of isobenzofuran-1(3h)-ones with the aid of silica-supported preyssler nanoparticles

Silica-supported Preyssler nanoparticles appear to be a new and efficient solid acid catalyst for an economical, and environmentally benign one-pot synthesis of 3-substituted phthalides.

Microwave-assisted solid acid-catalyzed one-pot synthesis of isobenzofuran-1(3H)-ones

A new, solid acid-catalyzed microwave-assisted environmentally benign synthesis of isobenzofuran-1(3H)-ones is described. Montmorillonite K-10 appeared to be an excellent catalyst for the condensation and successive lactonization reactions. Reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl and cyclic ketones was initiated by microwave irradiation and occurred in one step. The reactions were complete in 10-30 minutes providing excellent yields (90-98%).

One-pot synthesis of 3-phenacylphthalides

Acid catalyzed condensation of phthalaldehydic acid (1) with aromatic methyl ketones (2) providing 3-phenacylphthalides (3) is described. Copyright Taylor & Francis, Inc.