19865-55-5

Usage

InChI:InChI=1/C14H13NO/c1-12-7-9-13(10-8-12)11-15(16)14-5-3-2-4-6-14/h2-11H,1H3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 100-65-2 N-Phenylhydroxylamine 
• 73662-56-3 C₁₄H₁₃NO*C₆N₄ 
• 2362-77-8 (4-methylbenzylidene)phenylamine 
• 586-96-9 Nitrosobenzene 
• 98-95-3 nitrobenzene 
• 99447-84-4 C₁₄H₁₃NO*C₈Cl₂N₂O₂ 

Downstream Products

• 29068-12-0 2-phenyl-6a-pyrrolidin-1-yl-3-p-tolyl-hexahydro-cyclopenta[d]isoxazole 
• 29068-02-8 2-phenyl-7a-pyrrolidin-1-yl-3-p-tolyl-octahydro-benzo[d]isoxazole 
• 92234-40-7 5-(1-imidazolyl)-3-(4-methylphenyl)-2-phenylisoxazolidine 
• 73662-64-3 2-phenyl-3-(p-tolyl)-5-(tricyanovinyl)-Δ⁴-1,2,4-oxadiazoline 
• 97585-04-1 ethyl (E)-3-(4-methylphenyl)acrylate 
• 495-48-7 azoxybenzene 
• 104-87-0 4-methyl-benzaldehyde 
• 98056-28-1 3-anilino-1,4-diphenylbutane-1,2,4-trione 
• 835-71-2 2-(4-methylphenyl)-1,3-benzoxazole 
• 2362-77-8 (4-methylbenzylidene)phenylamine 
• 83871-63-0 N₁,N₂-di(phenyl)-1,2-di(4'-methylphenyl)-1,2-ethanediamine 
• 111663-86-6 1,3-diphenyl-4-(p-tolyl)azetidin-2-one 
• 888735-43-1 (3S,4S)-4-(4-methylphenyl)-1,3-diphenyl-2-azetidinone 
• 1401091-72-2 N-phenyl-N-(2-phenyl-1-(p-tolyl)ethyl)-O-(trimethylsilyl)hydroxylamine 

Relevant academic research and scientific papers

LIC-KOR promoted nitrone reactivity: Stereoselective synthesis of highly conjugated imines and secondary amines

The reactivity of metalated alkoxy-1,3-dienes and α-aryl-N-phenylnitrones in the presence of LIC-KOR base, equimolar mixture of alkyllithium (LIC) and potassium alcoxides (KOR), (Schlosser, 1994) [1] has been studied. A cascade reaction involving a E1cb p

Synthesis of 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones via 1,3-dipolar cycloaddition reaction involving (Z)-C-aryl-N-phenylnitrones

[Figure not available: see fulltext.] The 1,3-dipolar cycloaddition of C-aryl-N-phenylnitrones to 7-arylmethylidene-6,7-dihydroindolizin-8(5H)-ones afforded novel 2′,3′,4′-triaryl-5,6-dihydro-8H-spiro[indolizine-7,5′-isoxazolidin]-8-ones in moderate yield

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.

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.

Synthesis and Antimicrobial Evaluation of New Pyrrolo-isoxazolidine Derivatives

In the present study, pyrrolo-isoxazolidines 3(a-l) and 4(a-e), 4g, 4i, 4j have been synthesized by using the 1,3-dipolar cycloaddition reactions of nitrones 1(a-l) with ester substituted N-aryl maleimide (2b). These heterocycles have been obtained in cis and trans diastereomeric forms. The structures of newly synthesized heterocycles have been confirmed from their spectroscopic parameters such as IR,1H NMR,13C NMR and ESI-MS. The in vitro antimicrobial evaluation of these compounds were also investigated. Most of the prepared heterocycles showed significant antimicrobial properties. C3-phenyl substituted products exhibited the remarkable antibacterial behaviours while C3-thienyl/furyl substituted heterocycles proved themselves potent antifungal agents.

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.

Copper-Catalyzed Synthesis of Polysubstituted Pyrroles through [3+1+1] Cycloaddition Reaction of Nitrones and Isocyanides

An efficient, copper-catalyzed [3+1+1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting polysubstituted pyrroles from easily available nitrones and α-acidic isocyanides. The given approach features a new mo

Trifluoromethyl Vinyl Sulfide: A Building Block for the Synthesis of CF3S-Containing Isoxazolidines

Trifluoromethyl vinyl sulfide, a potential building block for pharmaceutically and agrochemically relevant products, is prepared and used for the first time in high-pressure-mediated 1,3-dipolar cycloaddition reactions with nitrones to synthesize (trifluoromethyl)sulfanyl isoxazolidines.

Coupling of N -Nosylhydrazones with Nitrosoarenes: Transition-Metal-Free Approach to (Z)- N -Arylnitrones

An efficient and transition-metal-free protocol for the synthesis of (Z)- N -arylnitrones from the direct coupling of N -nosylhydrazones with nitrosoarenes under mild conditions is described. The protocol is compatible with a wide range of functional groups placed on both the reagents and provided the corresponding nitrones in good to excellent yields by simple recrystallization process. The use of these 1,3-dipoles for the synthesis of substituted indoles is elaborated for 2,3-diphenyl-1 H -indole.

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.