69322-22-1

Upstream product

• 122-00-9 para-methylacetophenone 
• 119-67-5 o-carboxybenzaldehyde 
• 1777-53-3 1-(p-tolyl)-2-(triphenylphosphoranylidene)ethanone 
• 1313821-98-5 2-((p-methylbenzoyl)vinyl)benzaldehyde 
• 619-41-0 4-(bromoacetyl)toluene 
• 4079-54-3 2-hydroxy-1-p-tolyl-ethanone 
• 703-59-3 homophthalic anhydride 
• 13422-78-1 3-oxo-3-p-toluoylpropanoic acid 
• 5337-93-9 4'-methylpropiophenone 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Organocatalytic, Chemoselective Hydrophosphenylation/oxa-Michael Addition Cascade toward Diastereo- and Enantioenriched 1,3-Dihydroisobenzofuryl Phosphonates

An efficient method for the construction of chiral C-P bond via an enantioselective 1,2-hydrophosphenylation followed by an oxa-Michael addition cascade of ortho-formyl chalcones has been developed. This provides the diastereoenriched (cis)-1,3-dihydroisobenzofuryl phosphonates with excellent enantioselectivities (up to >99%). The origin of enantio- and diastereoselectivity is induced by using a chiral bifunctional organocatalyst. Further, functionalization to highly enantioselective 3-substituted phthalides has also been demonstrated.

Catalytic Asymmetric Conjugate Addition of Carboxylic Acids via Oxa-Michael Reaction of Peroxy Hemiacetals followed by Kornblum DeLaMare Fragmentation

Disclosed herein an overall methodology constitutes an equivalent to the long sought after enantioselective intramolecular oxa-Michael (IOM) reaction of carboxylic acids. An organocatalyzed IOM reaction of in situ formed peroxy hemiacetals followed by a K

Iridium/Copper-Catalyzed Oxidative C?H/O?H Annulation of Benzoic Acids with Saturated Ketones for Accessing 3-Substituted Phthalides

A catalytic annulation cascade is achieved that affords an efficient access to phthalides from readily available benzoic acids and saturated ketones. The reaction is catalyzed by a bimetallic Ir/Cu system and proceeds via the combination of Cu-catalyzed dehydrogenation of ketones and Ir-catalyzed direct C?H functionalization under the assistance of the weakly coordinating carboxyl followed by the β?H elimination and intramolecular Michael addition. This method shows a broad scope of substrates and good functional group tolerance. The protocol furnishes an alternative strategy for the construction of diverse 3-substituted phthalides.

Synthesis of 1-(3H)isobenzofuranone compounds by tin powder promoted cascade condensation reaction

An efficient approach for the construction of phthalide compounds is developed through tin powder mediated cascade condensation reaction of 2-formylbenzoic acids with allyl bromides or α-bromoketone under mild reaction conditions. This method is easy to operate and can tolerate various functional groups to give the corresponding phthalides in good to excellent yields. The phthalides produced from α-bromoketone can be further transformed to 3,3a-dihydro-8H-pyrazolo[5, l-a]isoindol-8-one and 8H-pyrazolo[5, l-a]isoindol-8-one.

Practical synthesis of 3-(2-arylethylidene)isoindolin-1-ones (analogues of AKS-182) and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones

A simple and practical method is reported for the synthesis of 3-(2-arylethylidene)isoindolin-1-ones and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones, proceeding with good to excellent yields and (E:Z) selectivity. This methodology involves the sequential reduction-dehydration reaction of readily obtained 3-(2-oxo-2-arylethyl)isoindolin-1-ones and 3-(2-oxo-2-arylethyl)isobenzofuran-1(3H)-ones followed by a base-catalyzed double bond isomerization with K2CO3 in acetonitrile. The development of a concise synthesis of AKS-182 has been achieved using this methodology.

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.

Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

Background: Phthalides are privileged constituents of numerous pharmaceuticals, natural products and agrochemicals and exhibit several biological and therapeutic activities. Therefore, the development of new, facile, and sustainable strategies for the construction of these moieties is highly desired. Results: A broad substrate scope for β-keto acids was found to be strongly compatible with this catalytic process, affording a wide variety of 3-substituted phthalides in good to excellent yields. Conclusion: A concise and efficient synthesis strategy of 3-substituted phthalides from 2-formylbenzoic acid and β-keto acids via a catalytic one-pot cascade reaction in glycerol has been accomplished.

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.