Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Reaction of Nucleophilic Reagents at the β-Position of 3-Bromo-4-nitropyridine N-Oxide
Eizo MatsumuraMasahiro Ariga
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1973 Volume 46 Issue 10 Pages 3144-3146

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Abstract

Some nucleophilic substitutions on the β-position of the pyridine nucleus were carried out. The reactions of 3-bromo-4-nitropyridine N-oxide(1) with diethyl sodiomalonate, ethyl sodiocyanoacetate, and ethyl sodioacetoacetate in diethyl carbonate or pyridine afforded 3-bis-(ethoxycarbonyl)methyl-4-nitropyridine N-oxide (2), 3-cyano(ethoxycarbonyl)methyl-4-nitropyridine N-oxide (3), and 3-acetyl(ethoxycarbonyl)methyl-4-nitropyridine N-oxide (4) respectively, and ethyl sodioacetoacetate, when treated at a higher temperature, gave 3-ethoxycarbonyl-2-methyl-furo(3,2-c)pyridine N-oxide (5). A probable mechanism of the reaction was presented.

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