- Zinc-promoted direct amination of nitropyridines with methoxyamine via vicarious nucleophilic substitution
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Direct animation of nitropyridines with methoxyamine in the presence of a stoichiometric amount of zinc(II) chloride under basic conditions proceeds to give aminonitropyridines.
- Seko, Shinzo,Miyake, Kunihito
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- Process for producing aminonitropyridines
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A process for producing an aminonitropyridine represented by the general formula [1], which comprises reacting a nitropyridine represented by the general formula [2] (wherein X1, X2 and X3 indicate a hydrogen atom, a halogen atom, a nitro group, a cyano group, an aryl group, an aromatic heterocycle or an alkyl group, etc.; Y is an oxygen atom; and n is 0 or 1) with an O-substituted hydroxylamine represented by the general formula [3] (wherein R4 is a hydrogen atom, an alkyl group, a cycloalkyl group or an aralkyl group; and R5 is an alkyl group or an aralkyl group) or a salt thereof in the presence of a base and a metal catalyst. STR1
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- SYNTHESES WITH AROMATIC NITRAMINES, V. PHOTOCHEMICAL REARRANGEMENT OF NITRAMINOPYRIDINES
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All three isomeric nitraminopyridines were photolysed in methanol with low-pressure mercury lamp (253.7 nm). 2-Nitraminopyridine yielded both 2-amino-3-nitro- and 2-amino-5-nitropyridines (isomer ratio 6.26 : 1). 3-Nitropyridine rearranged into both 4-nitro- and 2-nitro-3-aminopyridines (isomer ratio 1.28 : 1), whereas 4-nitraminopyridine gave 3-nitro-4-aminopyridine as the sole product. 1-Methyl-2-nitriminopyridine did not rearrange under the conditions applied, but 1-methyl-4-nitriminopyridine gave 3-nitro-4-methylaminopyridine.The latest product was also obtained when the same starting material was rearranged in conc. sulfuric acid.
- Sepiol, J.,Tomasik, P.
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p. 159 - 164
(2007/10/02)
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