20914-69-6

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 12, p. 107, 1975 DOI: 10.1002/jhet.5570120118

InChI:InChI=1/C6H6N4/c1-5-8-6-4-7-2-3-10(6)9-5/h2-4H,1H3

Upstream product

• 21352-21-6 2-(N-acetylamino)pyrazine 
• 36016-40-7 mesitylenesulfonylhydroxylamine 
• 68675-32-1 N,N-dimethyl-N'-pyrazin-2-yl-acetamidine 
• 83412-71-9 N-(pyrazin-2 yl) acetamide oxime 

Relevant academic research and scientific papers

Regioselectivity in the amination of azines: Reaction of pyrazine derivatives with O-mesitylenesulfonylhydroxylamine

Treatment of 2-X-substituted pyrazines [X = H, Me, Et, Pr, i-Pr, t-Bu, MeCH(OH), H2N, AcNH] with O-mesitylenesulfonylhydroxylamine gave the corresponding 2-X- and 3-X-(1-amino)pyrazin-1-ium mesitylenesulfonates. 2-Alkylpyrazines (X = Me, Et, Pr, i-Pr) displayed a correlation between the logarithms of the concentration ratio of 2- and 3-substituted cations and substituent steric constants. Wider series of substituted pyrazines [X = H, Me, Et, Pr, i-Pr, MeCH(OH), H2N, AcNH] conformed to a multiparameter correlation between the logarithms of the concentration ratio of 2- and 3-substituted cations, on the one hand, and substituent constants σI, σR?, and E s?, on the other. The obtained data on the regioselectivity of amination of pyrazines were interpreted in terms of DFT/PBE/3Z quantum-chemical calculations. Pleiades Publishing, Ltd., 2011.

Regioselectivity in 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine

The regioselectivity of 2-X-pyrazine aminations by O-mesitylenesulfonylhydroxylamine was studied experimentally and the results are discussed from the viewpoint of electronic and steric factors. DFT calculations are consistent with the reaction proceeding according to an SN2 mechanism.

Quinoline derivatives as neurokinin receptor antagonists

The present invention relates to substituted quinoline hydrazides of Formula (I): wherein R1, R2, R3, R4, R5, X, Y and Z are defined herein, pharmaceutical compositions comprising them and their use in treating diseases mediated by neurokinin-2 and/or neurokinin-3 (NK-3) receptors. These compounds can thus be used in methods of treatment to suppress and treat such disorders.

Reactions of N-Heteroarylformamide Oximes and N-Heteroarylacetamide Oximes with N,N-Dimethylformamide Dimethyl Acetal. Synthesis of 2-Methyl-s-triazoloazines and N-Methylcyanoaminoazines

N-Heteroarylformamide oximes 3 (R = H) were converted with N,N-dimethylformamide dimethyl acetal (DMFDMA) into N-heteroaryl-N-methylcyanoamino compounds 5, as the main products.In some instances N-heteroarylcyanoamino compounds 4, cyanoimino compounds 7, and some other products, such as 9 and 10 were also formed.On the other hand, N-heteroarylacetamide oximes 3 (R = CH3) were cyclized under the same reaction conditions into 2-methyl-s-triazoloazines (6).N-Heteroarylacetamide O-methyl oximes 11 and 12 were prepared from the corresponding acetamidines 2 (R = CH3) and O-methylhydroxylamine.