20147-40-4

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 586-96-9 Nitrosobenzene 
• 98-95-3 nitrobenzene 
• 100-65-2 N-Phenylhydroxylamine 

Downstream Products

• 68752-92-1 2-phenyl-3,5-di-pyridin-2-yl-isoxazolidine-4,4-dicarboxylic acid diethyl ester 
• 1435517-43-3 (R,E)-N-benzyl-4-methyl-N-((2-phenyl-3-(pyridin-2-yl)isoxazolidin-4-ylidene)methyl)benzenesulfonamide 
• 68752-88-5 4-cyano-2-phenyl-3,5-di-pyridin-2-yl-isoxazolidine-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Visible-Light-Photocatalyzed Reductions of N-Heterocyclic Nitroaryls to Anilines Utilizing Ascorbic Acid Reductant

A photoreductive protocol utilizing [Ru(bpy)3]2+ photocatalyst, blue light LEDs, and ascorbic acid (AscH2) has been developed to reduce nitro N-heteroaryls to the corresponding anilines. Based on experimental and computational results and previous studies, we propose that the reaction proceeds via proton-coupled electron transfer between AscH2, photocatalyst, and the nitro N-heteroaryl. The method offers a green catalytic procedure to reduce, e.g., 4-/8-nitroquinolines to the corresponding aminoquinolines, substructures present in important antimalarial drugs.

Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide

A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.

Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones

Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Br?nsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.

MODIFIED POLYMER, RUBBER COMPOSITION AND PNEUMATIC TIRE

The purpose of the present invention is to provide a modified polymer that significantly reduces heat build-up due to the modification when the modified polymer is formed into a rubber composition, a rubber composition containing the modified polymer, and

Rhodium-catalyzed cyclization of diynes with nitrones: A formal [2+2+5] approach to bridged eight-membered heterocycles

N-aryl-substituted nitrones were employed as fiveatom coupling partners in the rhodium-catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic C-H activation of the N-aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight-membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles,.

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.