70976-24-8

Upstream product

• 70977-28-5 C₉H₁₀N₂O₄ 
• 637-69-4 4-Methoxystyrene 
• 540-80-7 tert.-butylnitrite 

Downstream Products

• 70976-51-1 3-(4-methoxy-phenyl)-4-nitro-1-oxa-2-aza-spiro[4.5]dec-2-ene 
• 70976-35-1 3,5t-bis-(4-methoxy-phenyl)-4r-nitro-4,5-dihydro-isoxazole 
• 70976-48-6 3-(4-methoxy-phenyl)-5,5-dimethyl-4-nitro-4,5-dihydro-isoxazole 
• 70976-37-3 4-[3-(4-methoxy-phenyl)-4c-nitro-4,5-dihydro-isoxazol-5r-yl]-N,N-dimethyl-aniline 
• 70976-50-0 3-(4-methoxy-phenyl)-4-nitro-1-oxa-2-aza-spiro[4.4]non-2-ene 
• 70976-28-2 2-[3-(4-methoxy-phenyl)-4t-nitro-4,5-dihydro-isoxazol-5r-yl]-phenol 
• 70976-26-0 3-(4-methoxy-phenyl)-4r-nitro-5t-phenyl-4,5-dihydro-isoxazole 
• 70976-30-6 3-(4-methoxy-phenyl)-4r-nitro-5t-(4-nitro-phenyl)-4,5-dihydro-isoxazole 
• 70976-32-8 3-(4-methoxy-phenyl)-4r-nitro-5t-(3-nitro-phenyl)-4,5-dihydro-isoxazole 

Relevant academic research and scientific papers

Water-controlled nitro-oximation of alkenes under catalyst-free conditions

A convenient and precise nitration and oximation of alkenes with tert-butyl nitrite has been reported, yielding α-nitro ketoximes in satisfactory yields with broad substrate generality and excellent stereoselectivity under mild conditions. Experiments indicate that tert-butyl nitrite serves as both NO and NO2 sources and water plays a key role in this difunctionalization reaction.

Preparation method of alpha-nitro ketoxime derivative

The invention belongs to the field of organic synthesis, and specifically discloses a preparation method of alpha-nitro ketoxime derivatives. The method comprises the steps of taking a styrene derivative of the formula I-1 as a reaction raw material and butyl nitrite as a nitration reagent, adding an assistant, and reacting with water as a solvent under the condition of air at room temperature to obtain the alpha-nitro ketoxime derivative of formula I, has the characteristics of low production cost, mild process conditions, high yield, and environmentally friendly effects, and is very suitable for industrial production. The reaction formula of the method is shown in the description.

Nitration-Oximization of Styrene Derivatives with tert-Butyl Nitrite: Synthesis of α-Nitrooximes

A highly efficient method for direct nitration-oximization of styrene derivatives using tert-butyl nitrite (t-BuONO) in DMSO was developed. The present method offers a convenient and practical approach for the synthesis of α-nitrooximes in moderate to high yields. The salient features entail mild reaction conditions, metal-free reagent, environmentally benign solvent and simple experimental procedure.

Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite

We have discovered that various α-nitro ketoximes can be synthesized in good yields starting from styrenes and tert-butyl nitrite. The success of the reaction was critically dependent on the use of a mixture solvent of dimethylsulfoxide and water. The reaction can tolerate a wide variety of substituents including electron-withdrawing and electron-donating groups.

Convenient synthesis of α-nitrooximes mediated by OXONE

A novel OXONE mediated direct difunctionalization of alkenes with NaNO2 in aqueous acetonitrile for the synthesis of α-nitrooximes was developed. The α-nitrooximes were readily prepared in moderate to high yields at room temperature under mild reaction conditions. The present protocol offers an easy and environmentally benign approach to access various α-nitrooximes derived from styrene derivatives.

Synthesis and tautomerization study of pseudonitrosites to 1,2-nitroximes

4-R-Substituted 2-nitro-1-nitrosoethylbenzenes (R = H, CH3, OCH3, Cl, F) have been synthesized under solvent-free conditions and the mechanism of their tautomerization to 2-isonitroso-1-nitro-2-phenylethanes have been investigated by 1H NMR spectroscopy.

New NO-donors with antithrombotic and vasodilating activities, Part 21. Pseudonitrosites and other azodioxides with vicinal electron acceptors.

Twelve vicinally substituted nitro-nitroso compounds (pseudonitrosites) were synthesized, nine of them for the first time. In the solid state the dimeric azodioxides are present. In the class of the pseudonitrosites 2a-h, all compounds exhibited comparatively strong antiplatelet activity in vitro (Born test, collagen). Four of them showed an IC50 below 10 microM, 2a being the most active substance with an IC50 = 2.1 microM. When administered orally to rats (60 mg/kg) small antithrombotic effects were observed. The pseudonitrosite 6d was the most active compound (18% inhibition in arterioles). The in vitro decomposition of 2a at 37 degrees C gave NO and N2O, indicating that the above pharmacological effects were mediated by an NO-dependent mechanism. The replacement of the nitro group in the pseudonitrosite partial structure by other electron acceptors i.e. acetyl, carboxyl, or acetyloxy groups leads to inactive (10a) or less active compounds (10b, e).