2011
DOI: 10.1007/s10593-011-0660-0
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NitropyridineS. 9*. Synthesis of substituted 3-amino-5-nitropyridines

Abstract: The discovery of bacteriostatic activity of Sulfidine was the stimulus for the study of the chemistry of isomeric aminopyridines with the objective of converting them into promising sulfamide preparations [2].Aminopyridines with nitrogroups on the pyridine nucleus have been insufficiently well studied, which is explained by their low accessibility. Exceptions are 2-amino-3-nitro-and 5-nitropyridines and their derivatives, which are accessible thanks to the activity of 2-aminopyridine to electrophilic substitut… Show more

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Cited by 4 publications
(4 citation statements)
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“…38 We returned to this reaction after developing a convenient method of synthesis of the initial 3-amino-5-nitropyridines 1, which were previously unknown. 39 The starting 3-benzoylamino-5-nitropyridines 2 were synthesized by benzoylation (SchottenBaumann reaction) of 3-amino-5-nitropyridines 1 with benzoyl chloride ( The necessary pyridinium salts 3a-e were obtained by alkylation of pyridines 2a-e with dimethyl sulfate and methyl fluorosulfonate. Hygroscopic pyridinium methyl sulfates were transformed into the less-soluble pyridinium perchlorates 3 by replacement of the methyl sulfate anion to perchlorate ( Table 2).…”
Section: Resultsmentioning
confidence: 99%
“…38 We returned to this reaction after developing a convenient method of synthesis of the initial 3-amino-5-nitropyridines 1, which were previously unknown. 39 The starting 3-benzoylamino-5-nitropyridines 2 were synthesized by benzoylation (SchottenBaumann reaction) of 3-amino-5-nitropyridines 1 with benzoyl chloride ( The necessary pyridinium salts 3a-e were obtained by alkylation of pyridines 2a-e with dimethyl sulfate and methyl fluorosulfonate. Hygroscopic pyridinium methyl sulfates were transformed into the less-soluble pyridinium perchlorates 3 by replacement of the methyl sulfate anion to perchlorate ( Table 2).…”
Section: Resultsmentioning
confidence: 99%
“…Pyridines ( 2a , 2b , 2c ) were synthesized via benzoylation of 3‐aminopyridines ( 1a , 1b , 1c ) (Schotten–Baumann reaction). 3‐Aminopyridines ( 1a , 1b , 1c ) were obtained earlier by different sextet rearrangements (Curtius, Hofmann, and Schmidt rearrangements) and described in our previous work . Pyridinium salts ( 3a , 3b , 3c ) were synthesized via alkylation of 3‐benzoylamino‐5‐nitropyridines ( 2a , 2b , 2c ) by dimethyl sulfate and fluorosulfuric acid methyl ester (Scheme ).…”
Section: Resultsmentioning
confidence: 99%
“…Monitoring of the course of reactions and purity of the compounds obtained was by TLC on Silufol UV‐254 plates. 3‐Aminopyridines ( 1a , 1b , 1c ) was synthesized according to the procedures described in .…”
Section: Methodsmentioning
confidence: 99%
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