2973-17-3

Usage

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 665, 1994 DOI: 10.1016/S0040-4039(00)75785-6

InChI:InChI=1/C7H7NO2/c1-2-5-8-6(9)3-4-7(8)10/h2-4H,1,5H2

Upstream product

• 6971-11-5 (3aRS,4SR,7RS,7aSR)-2-allyl-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione 
• 541-59-3 maleiimide 
• 107-18-6 allyl alcohol 
• 925-02-0 N-allyl-maleamic acid 
• 108-31-6 maleic anhydride 
• 107-11-9 1-amino-2-propene 
• 32620-89-6 C₁₁H₁₁NO₃ 

Downstream Products

• 88121-63-5 (3aS,4S,9aR,9bR)-2-Allyl-4-benzoyl-3a,4,9a,9b-tetrahydro-pyrrolo[3,4-a]indolizine-1,3-dione 
• 1364041-43-9 (R)-methyl 2-((R)-1-allyl-2,5-dioxopyrrolidin-3-yl)-2-isocyano-2-phenylacetate 
• 54433-51-1 1-allyl-3-phenyl-pyrrolidine-2,5-dione 
• 2555-14-8 N-allylsuccinimide 
• 625852-58-6 (-)-(R)-6,7,8,8a-tetrahydro-5H-indolizin-3-one 

Relevant academic research and scientific papers

Copolymerization of N-vinylpyrrolidone with new allyl monomers

Radical copolymerization of N-vinylpyrrolidone with diallylacylhydrazines, 2,2-diallyl-1,1,3,3-tetraethylguanidinium chloride, N-allyl-2-azanorborn-5-ene, and N-allylmaleimide in the bulk and in organic solvents was studied. The kinetic features of the reactions were examined, the structures of the copolymers obtained were determined, and their physicochemical and biological properties were studied. Pleiades Publishing, Ltd., 2010.

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 quaternary stereogenic centres via stereoselective intermolecular Friedel-Crafts reactions

Highly stereoselective Friedel-Crafts reactions have been performed using a chiral anthracene template to control the selectivity of the reaction. In the case of additions to fully substituted N-acyliminium ions, competitive elimination and condensation r

Photochemical Reaction of N,N-Dimethylanilines with N-Substituted Maleimides Utilizing Benzaldehyde as the Photoinitiator

Photoorganocatalysis constitutes a powerful domain of photochemistry and organic synthesis. The scaffold of pyrrolo[3,4-c]quinolinoles exhibits interesting and potent inhibition against various enzymes, making them really promising pharmaceutical targets. Herein, we describe a photochemical methodology for the reaction of N,N-dimethylanilines with N-substituted maleimides, utilizing benzaldehyde as the photoinitiator. A variety of substituted N,N-dimethylanilines and N-substituted maleimides were converted into the corresponding adducts in moderate to high yields.

Chemo- And diastereoselectivities in the electrochemical reduction of maleimides

The electrochemical cathodic reduction of cyclic imides (maleimides) to succinimides can be achieved chemoselectively in the presence of alkene, alkyne, and benzyl groups. The efficiency of the system was demonstrated by using a 3D electrode in a continuous flow reactor. The reduction of 3,4-dimethylmaleimides to the corresponding succinimides proceeds with a 3:2 diastereomeric ratio, which is independent of the nitrogen substituent and electrode surface area. The stereoselectivity of the process was rationalized by using DFT calculations, involving an acid-catalyzed tautomerization of a half-enol occurring through a double hydrogen-transfer mechanism.

Experimental and theoretical studies of selective thiol-ene and thiol-yne click reactions involving N -substituted maleimides

A combination of experimental and computational methods has been used to understand the reactivity and selectivity of orthogonal thiol-ene and thiol-yne ″click″ reactions involving N-allyl maleimide (1) and N-propargyl maleimide (2). Representative thiols methyl-3-mercaptopropionate and β-mercaptoethanol are shown to add exclusively and quantitatively to the electron poor maleimide alkene of 1 and 2 under base (Et3N) initiated thiol-Michael conditions. Subsequent radical-mediated thiol-ene or thiol-yne reactions can be carried out to further functionalize the remaining allyl or propargyl moieties in near quantitative yields (>95%). Selectivity, however, can only be achieved when base-initiated thiol-Michael reactions are carried out first, as radical-mediated reactions between equimolar amounts of thiol and N-substituted maleimides give complex mixtures of products. CBS-QB3 calculations have been used to investigate the energetics and kinetics of reactions between a representative thiol (methyl mercaptan) with N-allyl and N-propargyl maleimide under both base-initiated and radical-mediated conditions. Calculations help elucidate the factors that underlie the selective base-initiated and nonselective radical-mediated thiol-ene/yne reactions. The results provide additional insights into how to design selective radical-mediated thiol-ene/yne reactions.

A silicone compound, photocurable liquid ink using the silicone compound, and method of manufacturing the ink

A silicone compound represented by the following Chemical Structure 1: where Y represents a substituted or non-substituted alkyl group having one to ten carbon atoms, X1, X2, and X3 independently represent methyl groups or any of the following Substituent

Synthesis on N-alkylated maleimides

A two step synthesis of N-alkylated maleimides is presented. This method allows for the use of widely available starting materials and produces maleimides in high purity and yields. The maleimide precursors are of interest for potential thermo- and photo-setting polymerization processes.

Microwave-induced One-pot Synthesis of N-carboxyalkyl Maleimides and Phthalimides

Maleic and phthalic anhydride condenses with amino acids and alkylamines under microwave irradiation to afford N-substituted maleimides and phthalimides in excellent yields.