75715-21-8

Upstream product

• 108-31-6 maleic anhydride 
• 542-92-7 cyclopenta-1,3-diene 
• 100-46-9 benzylamine 
• 129-64-6 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 
• 100-39-0 benzyl bromide 
• 6265-30-1 (1R,2S,6R,7S)-4-azatricyclo[5.2.1.0(2,6)]dec-8-ene-3,5-dione 
• 100-44-7 benzyl chloride 
• 106754-07-8 endo-3-(N-benzylcarbamoyl)bicyclo[2.2.1]hept-5-ene-endo-2-carboxylic acid 
• 1251910-89-0 C₁₇H₁₃NO₂ 

Downstream Products

• 171897-52-2 2-benzyl-1,3,r-3a,4,7,c-7a-hexahydro-t-4,t-7-methanoisoindole 
• 21449-84-3 2-benzyl-5c,6c-epoxy-(3ac,7ac)-hexahydro-4r,7c-methano-isoindole-1,3-dione 

Relevant academic research and scientific papers

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

A study exploring halofluorination and fluoroselenation of some cyclic olefins, such as diesters, imides, and lactams with varied functionalization patterns and different structural architectures is described. The synthetic methodologies were based on electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with Deoxo-Fluor. The fluorine-containing products thus obtained were subjected to elimination reactions, yielding various fluorine-containing small-molecular entities.

Tandem ROMP-hydrogenation with a third-generation grubbs catalyst

Tandem ROMP-hydrogenation enables efficient access to saturated, functionalized "ROMP polyolefins". Of the Grubbs-class initiators 1-3, only third-generation catalyst 3 enables efficient ROMP of sterically demanding norbornenes with precise specification of chain lengths. Unlike 1 and 2, however, 3 decomposes rapidly during subsequent hydrogenation. By trapping the propagating species with PCy3 immediately following ROMP, we generate a Ru-terminated chain identical to that formed from 2 and exhibiting equivalent hydrogenation activity. The remarkable ROMP efficiency of 3 can thus be integrated with the high hydrogenation activity of 2, providing efficient access to chain-length-precise, functionalized polyolefins. Copyright

Synthesis of 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione derivatives as lead scaffolds for neuroprotective agents

Neurodegenerative disorders are characterised by progressive loss of neuronal functions. Of the proposed mechanisms, excitotoxicity, mediated by prolonged glutamate activation and calcium overload, is prominent. NGP1-01, a polycyclic cage amine, and tricyclo[6.2.1.02,7]undec-9-ene-3,6-dione have been shown to display calcium-modulating properties. In this study, we synthesised structurally-related 4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione as the base scaffold, and incorporated various functional moieties through aminolysis, to afford a series of imide derivatives. All final compounds were obtained in yields between 47-97% and their structures were confirmed by NMR, IR and MS. These structurally-related derivatives could potentially act as neuroprotective agents. Additionally, their synthetic versatilities could make them precursors, as lead compounds, to potential pharmacologically-active agents.

Mechanochemical N-alkylation of imides

The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.

Mechanochemical Grinding Diels-Alder Reaction: Highly Efficient and Rapid Access to Bi-, Tri-, and Tetracyclic Systems

Grinding of various electron-deficient dienophiles with diverse dienes in a pestle and mortar for 1-15 minutes afforded the corresponding Diels-Alder adducts in quantitative yields under catalyst-free and solvent-free conditions, without the necessity for

Polyethylene as a Cosolvent and Catalyst Support in Ring-Opening Metathesis Polymerization

Polyethylene oligomers (PEOlig) can be used as cosolvents and sometimes soluble catalyst supports in ring-opening metathesis polymerization (ROMP) reactions. As a catalyst support, this polyolefin serves as an N-heterocyclic carbene ligand for a ROMP catalyst, making it soluble at 70 °C and insoluble at room temperature. As a cosolvent, unfunctionalized PE oligomers facilitate quantitative separation of PEOlig-bound Ru-catalyst residues from polymer products. In these cases, the insolubility of the unfunctionalized polyethylene (Polywax) and its entrapment of the PEOlig-supported Ru residue in the product phase at room temperature afford ROMP products with Ru contamination lower than other procedures that use soluble catalysts. These separations require only physical processes to separate the product and catalyst residues - no additional solvents are necessary. Control experiments suggest that most (ca. 90%) of the Ru leaching that is seen results from Ru byproducts formed in the vinyl ether quenching step and not from the polymerization processes involving the PEOlig-supported Ru complex. (Chemical Equation Presented).

RCM approach to complex polycyclic α-hydroxy γ-lactams: Synthesis of indolizinones and pyrroloazepinones

The allylmagnesium chloride addition/RCM sequence on N-alkenyl-substituted imides provides a mild access to indolizinone and pyrroloazepinone derivatives with the α-hydroxy-γ-lactam framework. The procedure can be applied to the asymmetric synthesis of this type of derivatives, by employing a 2-exo-hydroxy-10-bornylsulfinyl group as a chiral auxiliary. Further functionality can be introduced at the angular position through an α-amidoalkylation reaction. The sequence of allylmagnesium chloride addition/RCM sequence using N-alkenyl-substituted imides provides mild access to indolizinone and pyrrolozepinone derivatives with an α-hydroxy-γ- lactam framework. Copyright

Synthesis of conformationally defined glutamic acid analogues from readily available Diels-Alder adducts

New amino acids, (±)-t-3,t-4-bis(carboxymethyl)-r-2- pyrrolidinecarboxylic acid (1d) and (±)-t-3a,t-6a-perhydro-r-1,t-4,t-6- cyclopenta[c]pyrroletricarboxylic acid (2), which possess relatively similar configurations to kainic acid, were synthesized from readily available Diels- Alder adducts.

A SYNTHESIS OF SUCCINIMIDES AND GLUTARIMIDES FROM CYCLIC ANHYDRIDES

The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence: (1) reaction with a primary amine, (2) conversion of the intermadiate monoamide to an N-hydroxysuccinimidyl ester using N,N'-disuccinimidyl oxalate