26820-68-8Relevant articles and documents
Practical amination of nitropyridones by silylation
Singer, Robert A.,Dore, Michael
supporting information, p. 1261 - 1264 (2013/01/03)
A practical method for coupling nitropyridones (1) with primary amines by treatment with hexamethyldisilazane has been developed, avoiding the use of hazardous reagents such as POCl3. The activation of the pyridone by a nitro group is necessary for efficient coupling, leading to aminonitropyridines (3) in good yields. Regioisomers other than 3-nitro-4-pyridone (1) were found to be substantially less reactive but would undergo coupling with primary amines.
Nucleophilic heteroaromatic substitution: Kinetics of the reactions of nitropyridines with aliphatic amines in dipolar aprotic solvents
Isanbor, Chukwuemeka,Emokpae, Thomas A.
, p. 125 - 135 (2008/09/18)
Rate data are reported for the reactions of 2-chloro-5-nitropyridine 2a, 2-chloro-3-nitropyridine 2b, and the corresponding 2-phenoxy derivatives 2c with n-butylamine, pyrrolidine and piperidine and 2d with n-butylamine and pyrrolidine in dimethyl sulfoxi
The effects of ring substituents and leaving groups on the kinetics of SNAr reactions of 1-halogeno- and 1-phenoxy-nitrobenzenes with aliphatic amines in acetonitrile
Crampton, Michael R.,Emokpae, Thomas A.,Isanbor, Chukwuemeka
, p. 1378 - 1383 (2008/09/18)
Rate constants are reported for the reactions of a series of 1-chloro-, 1-fluoro- and 1-phenoxy-nitrobenzenes activated by CF3 or CN groups or by ring-nitrogen with n-butylamine, pyrrolidine or piperidine in acetonitrile. The results are compar
Electrochemical synthesis of nitroanilines
Gallardo, Iluminada,Guirado, Gonzalo,Marquet, Jordi
, p. 251 - 259 (2007/10/03)
Alkylamines and amides are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Useful yields (15-85%) are achieved in a simple direct and regioselective amination process. The synthetic method has been examined in the absence and presence of external bases, used to promote the first step of the nucleophilic aromatic substitution reaction, i.e. the nucleophilic attack. In both cases, good results were obtained. The unreacted starting material can easily be recovered at the end of the electrochemical oxidation process. This new method represents an environmentally favourable route to amino- and amido-substituted nitroaromatic compounds.
Synthesis of N-alkoxybenzimidazoles and N-alkoxypyrimidazoles
Gardiner, John M,Goss, Andrew D,Majid, Tahir,Morley, Andrew D,Pritchard, Robin G,Warren, John E
, p. 7707 - 7710 (2007/10/03)
A variety of novel N-alkoxy aromatic-fused imidazoles have been prepared in a simple two-step process from 2-fluoro nitroaromatics and 2-chloro-3-nitropyridine. The imidazole forming step involves tandem heterocyclisation and O-alkylation with an in situ alkylating agent, and supports prior mechanistic proposals. Additional mechanistic experiments are described. The protocol is versatile with respect to both substrate halo-nitro aromatics and to the nature of the added electrophile (halides) used in the second step, and thereby significantly extends the scope of this reaction and its applicability to diverse synthesis. This methodology can also be used to generate various types of novel N-alkoxypyrimidazoles (4-deazapurine analogues), and an X-ray structure of one such pyrimidazole is presented.
The oxidative amination of 3-nitropyridines
Bakke, Jan M,Svensen, Harald
, p. 4393 - 4395 (2007/10/03)
3-Nitropyridine was reacted with ammonia or alkylamines and KMnO4 under several different conditions. Substitutions in the para position to the nitro group were obtained with high regioselectivity: with ammonia, 2-amino-5-nitropyridine (66%), w
1H and 13C NMR Studies of Substituted Nitropyridines and Nitrobenzenes
Nudelman, N. S.,Cerdeira, S. B.
, p. 507 - 511 (2007/10/02)
The 1H and 13C NMR spectra of 3-nitro-, 5-nitro- and 3,5-dinitro-2-methoxypyridines have been determined.The results show the preferred cis conformation for the 2-methoxy group, and the importance of steric repulsion between the oxygen atom of this group
