4667-83-8

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General Description

2-(furan-2-ylmethyl)isoindoline-1,3-dione, also known as isoindoline-1,3-dione, is a complex organic compound with a molecular formula of C14H9NO3. It is a heterocyclic compound containing a furan ring and an isoindoline-1,3-dione ring, and is commonly used in organic synthesis and pharmaceutical research. The compound has potential applications in the development of new drugs and the production of organic materials due to its unique structural and chemical properties. Additionally, it has been studied for its antioxidant and anti-inflammatory properties, making it a promising candidate for further research into its potential medical applications.

Upstream product

• 85-44-9 phthalic anhydride 
• 617-89-0 furan-2-ylmethanamine 

Downstream Products

• 1028744-99-1 C₃₃H₂₁ClN₂O₆ 
• 1028745-13-2 C₃₃H₂₁N₃O₈ 
• 1028745-04-1 C₃₃H₂₁N₃O₈ 
• 1028744-91-3 C₃₃H₂₂N₂O₆ 
• 1028745-18-7 C₃₅H₂₆N₂O₈ 
• 1028744-95-7 C₃₃H₂₁BrN₂O₆ 
• 116750-06-2 5-(1,3-dioxo-2,3-dihydro-1H-2-isoindolylmethyl)-2-furaldehyde 
• 1028745-08-5 2-(5-{4-N,N-dimethylaminophenyl[5-(1,3-dioxo-2,3-dihydro-1H-2-isoindolylmethyl)-2-furyl]methyl}-2-furylmethyl)-1,3-isoindolinedione 

Relevant academic research and scientific papers

Preparation method of 5 -aminolevulinic acid hydrochloride intermediate (by machine translation)

The invention relates to a preparation method of 5 -aminolevulinic acid hydrochloride intermediate, which belongs to the field of pharmaceutical compound synthesis and provides a 5 -aminolevulinic acid hydrochloride intermediate preparation method which comprises the following technical points: (a), (1) or (2) compound in reaction solvent a, oxidizing agent a, compound of formula (5); or process b) wherein the compound of formula (6) or formula (3 4) is obtained under the action of a reaction solvent b and an oxidizing agent b 6. The compound of formula (6) is then purified to give 5 -aminolevulinic acid hydrochloride by an acidic hydrolysis deprotecting group, or a direct acidic hydrolysis deprotecting group. The environment-friendly oxidation reagent is adopted, the quality requirement of high-quality medicine raw materials can be met at the same time, the production efficiency can be improved, and the requirement of industrial large-scale production can be met. (by machine translation)

Transition Metal-Free Reduction of Activated Alkenes Using a Living Microorganism

Microorganisms can be programmed to perform chemical synthesis via metabolic engineering. However, despite an increasing interest in the use of de novo metabolic pathways and designer whole-cells for small molecule synthesis, the inherent synthetic capabilities of native microorganisms remain underexplored. Herein, we report the use of unmodified E. coli BL21(DE3) cells for the reduction of keto-acrylic compounds and apply this whole-cell biotransformation to the synthesis of aminolevulinic acid from a lignin-derived feedstock. The reduction reaction is rapid, chemo-, and enantioselective, occurs under mild conditions (37 °C, aqueous media), and requires no toxic transition metals or external reductants. This study demonstrates the remarkable promiscuity of central metabolism in bacterial cells and how these processes can be leveraged for synthetic chemistry without the need for genetic manipulation.

Alkoxide-Catalyzed Hydrosilylation of Cyclic Imides to Isoquinolines via Tandem Reduction and Rearrangement

An alkoxide-catalyzed hydrosilylation of cyclic imides to isoquinolines was realized via tandem reduction and rearrangement. Using TMSOK as the catalyst and (EtO)2MeSiH as the reductant, a series of cyclic imides containing different functional groups were reduced to the corresponding 3-aryl isoquinolines in moderate to good yields. The scenario of the reaction pathway was supposed to involve the reduction of imides to ω-hydroxylactams, which underwent rearrangement in the presence of a base catalyst, and then the carbonyl reduction, followed by siloxy elimination.

An efficient synthesis of N-substituted phthalimides using SiO2-tpy-Nb as heterogeneous and reusable catalyst

A novel and efficient heterogeneous catalyst SiO2-tpy-Nb was developed, and its application in the preparation of N-substituted phthalimides from o-phthalic acids or anhydrides with amines provides the desired products in good to excellent yields. The catalyst was stable and recoverable for eight consecutive cycles without a significant loss in its activity. Furthermore, the catalyst is applicable in continuous flow which indicates its potential utilization in industrialization.

Tandem Mannich/Diels-Alder reactions for the synthesis of indole compound libraries

A tandem Mannich/Diels-Alder sequence for the synthesis of small-molecule libraries with an indolyl-octahydro-3a,6-epoxy-isoindole core structure is demonstrated in this study. Representative diversification examples based on this scaffold were performed, and a library is being produced within the European Lead Factory (ELF) Consortium.

Furan ring opening-pyrrole ring closure: Simple route to 5-alkyl-2-(aminomethyl)pyrroles

A simple route to 5-alkyl-2-(aminomethyl)pyrroles is proposed that is based on hydrolytic ring opening of 5-alkylfurfurylamines followed by pyrrole ring closure under Paal-Knorr conditions. Georg Thieme Verlag Stuttgart New York.

Synthesis of amines of the di- and trifurylmethane series

Methods are proposed for the synthesis of amines of the di-and trifurylmethane series-prospective compounds for the production of polymers and macrocyclic molecules-on the basis of 2-(2-furylmethyl)-1,3-isoindolinedione.

DIARYL SUBSTITUTED ALKANES

The instant invention provides compounds of Formula (II) which are 5-lipoxygenase activating protein inhibitors. Compounds of Formula (II) are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.

Piperazinylalkyl Heterocycles as Potential Antipsychotic Agents

We recently reported on a series of pyrrole Mannich bases orally active in inhibiting the conditioned avoidance response (CAR) in rats.These compounds exhibit affinity for both D2 and 5-HT1A receptors, and some are noncataleptogenic.Such a profile suggest that they may be potential antipsychotic agents which lack the propensity for causing extrapyramidal side effects and tardive dyskinesias in humans.One of these compounds, 1--1-piperazinyl>methyl>-1H-pyrrol-2-yl>methyl>-2-piperidinone (RWJ 25730, 1), was chosen for further development but found to be unstable in dilute acid.In order to improve stability, we replaced the pyrrole methylene linkage to the piperazine ring with ethylene, employed ethylene and dicarbonyl as linkers between the lactam and the pyrrole ring, placed electron-withdrawing groups on the pyrrole ring, and substituted acyclic amide for lactam.In addition, we replaced the pyrrole segment with other heterocycles including thiophene, furan, isoxazole, isoxazoline, and pyridine.Generally, replacemcent of the N-methylpyrrole segment with thiophene, furan, isoxazoline, or pyridine afforded compounds equipotent with 1 in CAR, which were more stable in dilute acid.In the case of side chain or lactam modifications, CAR activity was significantly decreased or abolished, with the exception of 6.For the most part, the modifications to 1 resulted in the decrease or loss of D2 receptor binding.However, within this series, 5-HT1A receptor binding was greatly increased, with thiophene 40 exhibiting an IC50 of 0.07 nM.The CAR activities of pyrroles 6 and 12, thiophene 40, furans 44-47, isoxazolines 49 and 50, pyridine 54 coupled with their weak or nonexistent D2 binding and strong 5-HT1A binding suggest that they may be acting via a nondopaminergic mechanism or that dopaminergic active metabolites are responsible.Pyrrole 6 and furans 44 and 47 show promise as antipsychotic agents based on their CAR activity, receptor-binding profile, and solution stability.