19064-76-7

Upstream product

• 4546-20-7 p-methoxyphenylhydroxylamine 
• 100-52-7 benzaldehyde 
• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 100-17-4 para-methoxynitrobenzene 
• 104-94-9 4-methoxy-aniline 
• 1137-96-8 N-(benzylidene)aniline N-oxide 
• 1516-21-8 4-methoxynitrosobenzene 
• 2876-13-3 N-benzylpyridinium chloride 
• 19064-77-8 C-phenyl-N-p-tolyl-nitrone 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 98-95-3 nitrobenzene 
• 97369-36-3 1,2,3,5-Tetrahydro-7-methyl-2-phenyl-3-phenylsulfonyl-4H-1-benzazepin-4-on 

Downstream Products

• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 1040389-88-5 C₂₆H₂₄N₂O₄ 
• 153463-27-5 (R)-3-[(3R,4S)-1-(4-Methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 434283-67-7 (3S,4S)-1-(4-methoxyphenyl)-3,4-diphenyl-2-azetidinone 
• 1215859-41-8 C₂₉H₂₇NO₆ 
• 1215859-43-0 C₃₀H₂₉NO₆ 
• 1253523-71-5 methyl 3-chloro-1-(4-methoxy-phenyl)-4-oxo-2-phenyl-piperidine-3-carboxylate 
• 1410876-88-8 C₄₄H₃₄N₂O₂ 

Relevant academic research and scientific papers

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

Regio-and stereoselectivity of [3+2] cycloaddition reaction of methacrolein with diarylnitrones catalyzed by chiral rhodium complex

Stereoselective 1,3-dipolar cycloadditions asymmetric reaction between C,N-diarylnitrones and methacrolein catalyzed by the aqueous complex [(C5Me5)Rh(DPPP*).(H2O)] (SbF6)2, (DPPP = bis 1,2- diphenylphosphinopropane) at -20 °C are described. We have succeeded in synthesizing nitrones described in the literature with good yields, and those, N-phenyl-Cphenylnitrones which are not described in the literature, with appreciable yields. The isoxazolidines formed from the condensation of these nitrones with methacrolein have been found to be new compounds. The resulting endoisoxazolidines are obtained in modest to high regioselectivity and with ee up to 91%.

Polyfunctionalized biaryls accessed by a one-pot nucleophilic aromatic substitution and sigmatropic rearrangement reaction cascade under mild conditions

A practical synthetic method has been developed for polyfunctionalized biaryls based on a facile one-pot nucleophilic aromatic substitution (SNAr) reaction and [5,5]- or [3,3]-sigmatropic rearrangement reaction cascade. Under mild basic conditions, N-arylhydroxylamines reacted with o-activated fluoro (het)arenes to form N,O-diarylhydroxylamine intermediates which underwent spontaneously selective [5,5]-sigmatropic rearrangement reaction to produce diverse functionalized 4-amino-4′-hydroxy-1,1′-biaryls. A sequential SNAr reaction and [3,3]-sigmatropic rearrangement took place between N-arylhydroxylamines and 2-fluoropyridine derivatives or 4-fluorobenzonitrile to afford functionalized 2-amino-2′-hydroxy-1,1′-biaryls. As invaluable and unique building blocks, the resulting biaryls were applied in the straightforward synthesis of N2,O2-coronarene, carbazole, aza- and diaza carbazole derivatives.

Gold-Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3-Sigmatropic Shift of an Initial Intermediate

Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species.

Regio-and stereoselectivity of [3+2] cycloaddition reaction of methacrolein with diarylnitrones catalyzed by chiral rhodium complex

Stereoselective 1,3-dipolar cycloadditions asymmetric reaction between C,N-diarylnitrones and methacrolein catalyzed by the aqueous complex [(C5Me5)Rh(DPPP*).(H2O)] (SbF6)2, (DPPP = bis 1,2-diphenylphosphinopropane) at -20 oC are described. We have succeeded in synthesizing nitrones described in the literature with good yields, and those, N-phenyl-Cphenylnitrones which are not described in the literature, with appreciable yields. The isoxazolidines formed from the condensation of these nitrones with methacrolein have been found to be new compounds. The resulting endoisoxazolidines are obtained in modest to high regioselectivity and with ee up to 91%.

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.

Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.

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 Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity

The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.

Preparation method for 3-chloro-4-alkoxyl aniline compounds

The invention relates to a preparation method for 3-chloro-4-alkoxyl aniline compounds; the compounds are key intermediates for synthesis of dyes, soft matters, histone deacetylase inhibitors and other precious drugs. Because of the difficulty of preparation, the market supply of the compounds is not enough, and the price is high. The invention provides the simple method adopting nitrone and oxalyl chloride as raw materials for reaction, wherein the nitrone is synthesized by 4-alkoxy nitrobenzene and benzaldehyde. The preparation method for the 3-chloro-4-alkoxyl aniline compounds has the advantages of cheap raw materials, wide market supply, simplified synthesis reaction conditions, low preparation cost and good industrial practical value.