2596-90-9

Upstream product

• 100-65-2 N-Phenylhydroxylamine 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 

Downstream Products

• 29068-04-0 N,N-dimethyl-4-(2-phenyl-7a-pyrrolidin-1-yl-octahydro-benzo[d]isoxazol-3-yl)-aniline 
• 70464-60-7 3ξ,5-bis-(4-dimethylamino-phenyl)-2-phenyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 95794-15-3 N¹-<4-(N,N-dimethylamino)phenyl>-N¹,N²-diphenylformamidine 
• 98056-28-1 3-anilino-1,4-diphenylbutane-1,2,4-trione 
• 98056-30-5 2-(4-N,N-dimethylaminophenyl)-4,5-dibenzoyl-3-phenyl-Δ⁴-oxazoline 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 130088-42-5 2-(4-Dimethylamino-phenyl)-3-oxy-benzoimidazol-1-ol 
• 29068-14-2 N,N-dimethyl-4-(2-phenyl-6a-pyrrolidin-1-yl-hexahydro-cyclopenta[d]isoxazol-3-yl)-aniline 
• 1020256-86-3 3-(4-(dimethylamino)phenyl)-4-methyl-2-phenylisoxazolidine-4-carboxaldehyde 
• 1360631-58-8 3-[4-(dimethylamino)phenyl]-2-phenyl-2,3-dihydrobenzo[d]isoxazole 

Relevant academic research and scientific papers

Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra

The compounds N-(benzylidene)-anilines XArCH=NArY (XBAY), N-(phenyl-ethylene)-anilines XArC(CH3)=NArY (XPEAY) and N-phenyl-α-phenylnitrones XArCH=N(O)ArY (XPNY) have bridging group CH=N, C(CH3)=N and CH=N(O) respectively, in which the C(CH3)=N has a side-group methyl CH3 at carbon end and the CH=N(O) has a side-group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm-1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results indicate: (1) There are no good linear relationships between the νmax of XBAYs and XPEAYs or XPNYs. (2) In case of a same set of X-Y group couples, the distribution of λmax of XPEAYs is larger than that of XPNYs. (3) The side-group CH3 makes the effect of σ(X) larger than that of σ(Y) on the νmax of XPEAYs, whereas the O atom makes the effect of σ(Y) larger than that of σ(X) on the νmax of XPNYs. (4) The cross-interaction between X and Y has important effect on the all νmax. However, the cross-interaction between CH3 and X/Y has not important effect on the νmax of XPEAY, and the cross-interaction between O and X/Y has not important effect on the νmax of XPNY. Copyright

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

Direct oxidative synthesis of nitrones from aldehydes and primary anilines using graphite oxide and Oxone

One-pot condensation/oxidation of aldehydes and primary anilines into nitrones using graphite oxide (GO) and Oxone as the oxidant under very mild reaction conditions is described. The proposed method provides a direct oxidative synthesis of various nitrones in good to excellent yields under metal-free conditions in short reaction times.

Copper(I)-catalyzed three component reaction of sulfonyl azide, alkyne, and nitrone cycloaddition/rearrangement cascades: A novel one-step synthesis of imidazolidin-4-ones

A novel one-pot azide-alkyne/ketenimine-nitrone cycloaddition sequence that is induced by copper(I) and allows the transformation of sulfonyl azides, alkynes, and nitrones to highly substituted imidazolidin-4-ones is described. The corresponding heterogeneous version utilizing Cu(I)-modified zeolites as recyclable heterogeneous catalysts shows marginally improved yield and diastereoselectivity.

Effect of substituents on spin density in benzimidazole nitronyl nitroxide radicals studied by electron spin resonance

Several novel benzimidazole-3-oxide-1-oxyl radicals with substituents at 5 and/or 6 position were synthesized. The ESR analysis of nitrogen hyperfine coupling constants (hfccs) revealed that substituents at 5 and 6-position affect the spin density to greater extent than substituents on the phenyl ring at 2-position. Density functional theory calculations of nitrogen hfccs were performed using several different Pople type basis sets, as well as double and triple zeta quality individual gauge for localized orbital (IGLO-II, IGLO-III) and electron paramagnetic resonance (EPR-II, EPR-II) basis sets. Experimental and theoretical hfccs are compared.

Synthesis and bioorthogonal coupling chemistry of a novel cyclopentenone-containing unnatural tyrosine analogue

Herein we report the synthesis of a novel amino acid with orthogonal functionality to the natural amino acid side chains. Tyrosine was O-alkylated with a cyclic 5-membered α,β-unsaturated ketone ring (5). We have established that this amino acid analogue can undergo cycloaddition reactions in aqueous media with in situ generated nitrones. Nitrone formation occurred by micellar catalysis can undergo aqueous 1,3-dipolar cycloaddition reactions with the unnatural Tyr. We also performed a linear free energy analysis of the one pot bioconjugation reaction in water using cyclopentenone as a model for the Tyr analogue and seven different aryl nitrones. We found that the Hammett ρ value was -0.94, suggesting that the reaction occurs in a concerted fashion with a slight positive charge buildup in the transition state. The Hammett ρ value also suggests that the bioconjugation reaction is tolerant of different substituents and thus may be useful for introducing novel functionality into peptides and proteins containing the Tyr analogue 5. The aqueous 1,3-dipolar cycloaddition reactions, that use nitrones to trap the O-alkylated Tyr 5, establish a novel strategy for rapid, water compatible bioconjugation reactions.

Evidence for the intermediacy of arylbenzylnitrenium ions in the thermal rearrangement of isoxazolidines derived from C,N-diarylnitrones and 2-morpholin-4-yl-acrylonitrile

In contrast to the diaryl, dialkyl, alkylaryl, and parent series, nothing is known about the generation and chemical behavior of arylbenzylnitrenium ions. Herein, we report that these species can be generated by a process involving an unprecedented therma

A clean clay catalysed synthesis of α,N-diarylnitrones

The first clean and the facile clay catalysed synthesis of α,N-diarylnitrones in good yield is reported.