76016-69-8

Upstream product

• 25854-41-5 dinitromethane sodium salt 
• 932-90-1 Benzaldoxime 
• 492-38-6 2-phenylacrylic acid 
• 698-16-8 benzohydroximoyl chloride 
• 536-74-3 phenylacetylene 
• 118898-87-6 2-phenyl-2-hydroxyiminoacetonitrile oxide 
• 29945-54-8 3-amino-4-phenylfuroxane 

Downstream Products

• 10349-14-1 4-phenyl-furazan-3-ylamine 
• 49558-03-4 4-nitro-3-phenylfuroxan 
• 873-67-6 benzonitrile oxide 
• 83276-88-4 nitroformonitrile oxide 
• 79750-02-0 3-methoxy-4-phenylfuroxan 

Relevant academic research and scientific papers

Straightforward Access to the Nitric Oxide Donor Azasydnone Scaffold by Cascade Reactions of Amines

A novel one-pot cascade method for the assembly of valuable NO-donor azasydnone scaffold has been developed. The construction strategy involves a diazotization/azo coupling/elimination/double rearrangement cascade sequence of readily available amines. The

Cytotoxic and apoptotic activity of nitrofuroxans on lymphoma cells

[Figure not available: see fulltext.] Five nitrofuroxans were synthesized and evaluated for their in vitro cytotoxicity against human lymphoma cells with different p53 status (Raji Burkitt's lymphoma and MOLT-4). The most promising compound exhibited IC50 values of 2.6–11.0 μM in MTT growth inhibitory assays. Flow cytometry data suggest that cytotoxic effects of given compounds in MOLT-4 cells are mediated by apoptosis via a p53-dependent pathway. Changes in nuclear morphology after treatment were evaluated by fluorescent microscopy after Hoechst staining. However, the studied nitrofuroxans did not induce apoptosis in Raji cells having the p53 mutant gene, thus suggesting a different mechanism of their action.

Dinitrogen trioxide-mediated domino process for the regioselective construction of 4-nitrofuroxans from acrylic acids

4-Nitrofuroxans (4-nitro-1,2,5-oxadiazole 2-oxides) were prepared by a dinitrogen trioxide-mediated domino reaction of acrylic acids under the action of NaNO2 excess in AcOH at room temperature. The reaction proceeds completely regioselectively and presents a new, simple, general, and safe method for the preparation of both 3-aryl- and 3-alkyl-4-nitrofuroxans available with difficulty before. A mechanism for the furoxan ring construction through a four-step one-pot protocol is proposed. The synthesized nitrofuroxans have been characterized by multinuclear NMR spectroscopy and X-ray powder diffraction.

Nitrosation of salts of 1-hydroxyimino-2,2-dinitro-1-R-ethanes, a novel method for the preparation of isomeric 3(4)-nitro-4(3)-R-furoxans

A novel general method for the synthesis of isomeric 3(4)-nitro-4(3)-R- furoxans is developed. 3-Nitro isomers were obtained by reaction of hydroximoyl chlorides with dinitromethane sodium salt followed by conversion of the resulting 1-substituted 1-hydroxyimino-2,2-dinitroethanes into dipotassium (or disodium salts) and their subsequent nitrosation with NaNO2 in AcOH or with N2O4. Thermal isomerization of 3-nitro isomers afforded 4-nitro isomers were prepared in high yields.

Regiospecific and Regioselective Synthesis of Isomeric Nitrofuroxanes from Unsaturated Compounds

Reaction of substituted unsaturated compounds with NaNO2 in acidic medium is studied and the reaction is shown to be a general method for preparation of isomeric nitrofuroxanes: β-nitrostyrenes and α-substituted acrylic acids form the corresponding 4-nitrofuroxanes (regiospecifically and regioselectively, respectively). The product of the reaction with phenylacetylene is 3-nitro-4-phenylfuroxan. Nitration of the aromatic ring in the synthesized 3-aryl-4-nitrofuroxanes is performed and the influence of the 4-nitro-furoxanyl fragment on the orientation of the NO2 groups in this reaction is revealed.

REACTIONS OF NITRILE OXIDES WITH NITROGEN OXIDES. 1. REACTIONS WITH NITROGEN TETROXIDE

We have studied the reaction of nitrile oxides with nitrogen tetroxide.It was shown that the reaction is selective: acetonitrile oxide yields ethylnitrolic acid, α-oximinophenylacetonitrile oxide gives a mixture of isomers of phenylnitrofuroxan, and aromatic nitrile oxides give aryltrinitromethanes.

Antimicrobial properties of some furazan and furoxan derivatives

Nitro and phenylsulfonyl derivatives of furazan and furoxan ring systems have been synthesized and tested in vitro for their antimicrobial properties. The nitro derivatives and the 4-phenyl-3-phenyl sulphonylfuroxan showed antibacterial, antifungal and antiprotozoal activity.