1459-12-7

Upstream product

• 75624-72-5 <4-(4-Nitrophenyl)-2,4-dioxobutyl>triphenylphosphonium-chlorid 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 1460-05-5 p-nitrophenylacetaldehyde 
• 18462-35-6 (E)-1-[2-bromovinyl]-4-nitrobenzene 
• 18462-34-5 (Z)-1-(2-bromovinyl)-4-nitrobenzene 
• 18436-62-9 1-(2,2-Dimethoxyethyl)-4-nitro-benzene 

Downstream Products

• 1253183-40-2 tert-butyl 3-(4-nitrobenzyl)-6,6a-dihydro-3aH-pyrrolo[3,4-d]isoxazole-5(4H)-carboxylate 
• 163759-15-7 N-hydroxy-2-(4-nitrophenyl)acetimidoyl chloride 
• 1338733-07-5 5-methyl-3-(4-nitrobenzyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole 
• 1338732-70-9 5-hydroxymethyl-3-(4-nitrobenzyl)-4,5-dihydroisoxazole methanesulfonate 
• 1338733-11-1 5-(N,N-dimethylaminomethyl)-3-(4-nitrobenzyl)-4,5-dihydroisoxazole hydrochloride 
• 1338732-78-7 5-(N,N-dimethylaminomethyl)-3-(4-nitrobenzyl)-4,5-dihydroisoxazole 
• 1338733-14-4 5-(N,N-dimethylaminomethyl)-3-(4-aminobenzyl)-4,5-dihydroisoxazole hydrochloride 
• 1338732-84-5 5-(N,N-dimethylaminomethyl)-3-(4-aminobenzyl)-4,5-dihydroisoxazole 
• 1338733-16-6 5-methyl-3-(4-nitrobenzyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole hydrochloride 
• 1338733-01-9 5-methyl-3-(4-nitrobenzyl)-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole 
• 1338733-19-9 3-(4-aminobenzyl)-5-methyl-4,5,6,6a-tetrahydro-3aHpyrrolo[3,4-d]isoxazole oxalate 

Relevant academic research and scientific papers

Synthesis of Nitriles from Aldoximes and Primary Amides Using XtalFluor-E

The dehydration reaction of aldoximes and amides for the synthesis of nitriles using [Et2NSF2]BF4 (XtalFluor-E) is described. Overall, the reaction proceeds rapidly (normally 1 h) at room temperature in an environmentally benign solvent (EtOAc) with only a slight excess of the dehydrating agent (1.1 equiv). A broad scope of nitriles can be prepared, including chiral nonracemic ones. In addition, in a number of cases, further purification of the nitrile after the workup was not required.

One-pot chemoenzymatic synthesis of aldoximes from primary alcohols in water

A new synthetic method for the one-pot preparation of aldoximes in water was developed; the method is based on the combination of the enzymatic oxidation of primary alcohols to aldehydes using different acetic acid bacteria and in situ condensation of the aldehydes with hydroxylamine.

Synthesis and biochemical evaluation of δ2-isoxazoline derivatives as DNA methyltransferase 1 inhibitors

A series of Δ2-isoxazoline constrained analogues of procaine/procainamide (7a-k and 8a-k) were prepared and their inhibitory activity against DNA methyltransferase 1 (DNMT1) was tested. Among them, derivative 7b is far more potent in vitro (IC50 = 150 μM) than other non-nucleoside inhibitors and also exhibits a strong and dose-dependent antiproliferative effect against HCT116 human colon carcinoma cells. The binding mode of 7b with the enzyme was also investigated by means of a simple competition assay as well as of docking simulations conducted using the recently published crystallographic structure of human DNMT1. On the basis of the findings, we assessed that the mode of inhibition of 7b is consistent with a competition with the cofactor and propose it as a novel lead compound for the development of non-nucleoside DNMT inhibitors.

Reactions with Organophosphorus Compounds, XLVI. Reactivity Umpolung of 1,3-Dioxo Compounds through Introduction of a Triphenylphosphonio Group. - Regioselective Syntheses of Isoxazoles and Pyrazoles from (2,4-Dioxoalkyl)triphenylphosphonium Salts

Phosphonium salts 2 and 6, upon deprotonation with BuLi and subsequent reaction with acyl halides, yield the γ-acyl derivatives 3 and 7, respectively, which on treatment with hydrochloric acid afford the corresponding (dioxoalkyl)phosphonium salts 4 and 8.Isoxazole derivatives 9 and 10 are formed regioselectivly from 4 and 8 with NH2OH*HCl, while with R-NH-NH2*HCl (R = H or C6H5) the pyrazole-containing phosphonium salts 14 and 15 are obtained in an analogous reaction.In each case the direction of cyclisation is different to the reactions of the corresponding non-phosphorus substituted 1,3-dioxo compounds.On treatment with aqueous NaOH 9 and 10 are cleaved to triphenylphosphane oxide and isoxazoles 11 and 12, while 14 and 15 yield the pyrazoles 16 and 17.Wittig reaction of 9a or 14a with aldehydes or ketones leads to the isoxazole olefins 13 or the pyrazole olefins 18, respectively.