28620-50-0

Upstream product

• 100-52-7 benzaldehyde 
• 91981-91-8 acetaldehyde phenylnitrone 
• 14371-10-9 (E)-3-phenylpropenal 
• 100-65-2 N-Phenylhydroxylamine 
• 98-95-3 nitrobenzene 
• 104-55-2 3-phenyl-propenal 
• 37056-75-0 cinnamaldehyde-(N-phenyl oxime ) 
• 20147-43-7 cis-5-ethoxy-3-phenyl-N-phenyl isoxazolidine 
• 19744-05-9 5-acetoxy-2,3-diphenyl-isoxazolidine 

Downstream Products

• 128918-86-5 Phenyl-[(E)-3-phenyl-1-phenylethynyl-prop-2-en-(Z)-ylidene]-amine 
• 20503-96-2 2-Phenyl-3-((E)-styryl)-isoxazolidine-5-carbonitrile 
• 20503-94-0 5-Chloromethyl-2-phenyl-3-((E)-styryl)-isoxazolidine 
• 340283-92-3 O-trimethylsilyl phenyl[3-(trans-1-phenyl-4,4,4-trifluorobut-1-enyl)]hydroxylamine 
• 113307-19-0 Ethyl (2Z,4E)-2-fluoro-5-phenyl-2,4-pentadienoate 
• 64723-89-3 Methyl N-phenylcinnamimidate 
• 24680-48-6 2-phenylimino-4t-phenyl-butene-⁽³⁾-nitrile 
• 120781-94-4 N-phenyl-3-β-cinnammyl-4-acetyl-5,5-dimethyl-isoxazolidine 
• 20503-96-2 2-phenyl-3-styryl-isoxazolidine-5-carbonitrile 
• 20503-94-0 5-chloromethyl-2-phenyl-3-styryl-isoxazolidine 
• 123003-85-0 1-phenyl-4-cinnamalazetidin-2-one 
• 1040389-82-9 C₂₆H₂₂N₂O₃ 
• 1360631-61-3 2-phenyl-3-((E)-2-phenylethenyl)-2,3-dihydrobenzo[d]isoxazole 

Relevant academic research and scientific papers

Catalyst-Free Regioselective [3+2] Cycloadditions of α,β-unsaturated N-arylnitrones with Alkenes to Access Functionalized Isoxazolidines: A DFT Study

The catalyst-free regioselective [3+2]-cycloaddition of α,β-unsaturated N-arylnitrones with alkenes are developed. The series of synthetically important functionalized isoxazolidines are prepared in good to excellent yields by step economic pathway under ligand and transition-metal-free conditions. The regioselective cycloaddition pathway supported by control experiment and computational study.

Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds

A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N2)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.

Cu(II)-catalyzed enantioselective 1,3-dipolar cycloaddition of nitrones with α, β-unsaturated acyl phosphonates

A highly enantioselective 1, 3-dipolar cycloaddition of nitrone with α, β-unsaturated acyl phosphonate was developed for the first time by using a chiral indane-bis(oxazoline)-copper(II) complex. The reaction proceeded smoothly under mild conditions to provide isoxazolidines with multi-stereocenters in good yields with high to excellent diastereo- (>20:1 dr) and enantioselectivities (up to 99% ee). The resulting products were readily converted to multi-functional isoxazolidines or γ-amino alcohol compounds.

Cu(i) mediated Kinugasa reactions of α,β-unsaturated nitrones: A facile, diastereoselective route to 3-(hydroxy/bromo)methyl-1-aryl-4-(-styryl)azetidin-2-ones

The manuscript describes a facile and highly diastereoselective synthesis of cis-3-(hydroxy/bromo)methyl-1-aryl-4-(-styryl)azetidin-2-ones via copper(i) mediated Kinugasa reactions of previously unexplored functionalized α,β-unsaturated nitrones. A variety of functionalized acetylenes and α,β-unsaturated nitrones were studied to yield cis-3-(hydroxy/bromo)methyl-1-aryl-4-(-styryl)azetidin-2-ones in good yields (82%).

Stereoselective synthesis of fluoroalkenoates and fluorinated isoxazolidinones: N-substituents governing the dual reactivity of nitrones

α-Fluoroalkenoates and 4-fluoro-5-isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones by the reactions between nitrones and α-fluoro-α-bromoacetate. By altering N-substituents in nitrones, (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones can be achieved, respectively, with high chemo- and stereoselectivities. Experimental and computational studies have been conducted to elucidate the reaction mechanisms. Linear free energy relationship studies further revealed that the N-substituent effects are primarily of electronic origin. Copyright

Urea-catalyzed construction of oxazinanes

Highly functionalized oxazinanes are efficiently prepared through urea-catalyzed formal [3 + 3] cycloaddition reactions of nitrones and nitrocyclopropane carboxylates. The reaction system is general with respect to both the nitrocyclopropane carboxylates and nitrones enabling the preparation of a large family of oxazinanes, typically in high yield. This method affords access to enantioenriched oxazinane products through chirality transfer from enantioenriched nitrocyclopropane carboxylates.

A highly stereoselective synthesis of chiral α-amino-β-lactams via the Kinugasa reaction employing ynamides

(Chemical Equation Presented) A highly stereoselective synthesis of chiral α-amino-β-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.

SYNTHESIS OF AVRAINVILLAMIDE, STEPHACIDIN B, AND ANALOGUES THEREOF

The syntheses of the natural products, avrainvillamide and stephacidin B, are provided. The α,β-unsaturated nitrone functionality of avrainvillamide and its 3- alkylidene-3H-indole 1 -oxide core is shown to covalently and reversibly bond to heteroatom-based nucleophiles. This capability may allow these molecules to bind active site nucleophiles and may provide the basis for designing potent and selective enayme inhibitors. Both avrainvillamide and its dimer stephacidin B have been reported to exhibit antiproliferative activity, and avrainvillamide has been reported to exhibit antimicrobial activity against multi-drug resistant bacteria. Avrainvillamide has been found to target cytoskeleton-linking membrane protein (CLIMP-63) thereby preventing cells from undergoing mitosis. The invention provides syntheses of these natural products as well as analogs of these natural products and their functional cores. The compounds of the invention may be used in the treatment of diseases such as cancer, autoimmune diseases, and bacterial infection.

Identification of a novel Michael acceptor group for the reversible addition of oxygen- and sulfur-based nucleophiles. Synthesis and reactivity of the 3-alkylidene-3H-indole 1-oxide function of Avrainvillamide

The 3-alkylidene-3H-indole 1-oxide functional group found in the naturally occurring alkaloid avrainvillamide has been synthesized by a cross coupling-reductive condensation sequence and found to undergo reversible addition of oxygen- and sulfur-based nucleophiles. Copyright

α-(trifluoromethyl)amine derivatives via nucleophilic trifluoromethylation of nitrones

(Trifluoromethyl)trimethylsilane (TMSCF3) reacts with nitrones to afford α-(trifluoromethyl)hydroxylamines protected as O-trimethylsilyl ethers. Potassium t-butoxide initiates the nucleophilic trifluoromethylation. The reaction works best with α,N-diaryl nitrones, and the conditions are compatible with a range of substituents on the aryl groups. Acidic deprotection of the nitrone/TMSCF3 adducts generates α-(trifluoromethyl)hydroxylamines. Catalytic hydrogenation of the adducts produces α-(trifluoromethyl)amines. Nitrone/TMSCF3 adducts with strong electron-withdrawing groups on the α-aryl ring or heterocyclic α-aryl groups undergo an elimination/addition sequence to generate α, α-bis(trifluoromethyl)amines. Nitrones with alkyl groups bound directly to the 1,3-dipolar moiety fail to react with TMSCF3, but trifluoromethylation of β,γ-unsaturated nitrones followed by reduction of the double bond can circumvent this limitation.