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Issue 0, 1981
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Synthetic applications of N–N linked heterocycles. Part 9. Preparation of α-(4-pyridyl)nitroalkanes and N-(4-pyridyl)azoles by regiospecific attack of nitroalkyl and azolyl anions on N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium salts

Abstract

Sodium salts of nitroalkanes and of azoles react with N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium salts (1)–(3) to give regiospecifically 1,4-dihydropyridines (12)–(14), (15), and (16) in high yields. Photolysis of the dihydropyridines gives α-(4-pyridyl)nitroalkanes (7)–(9) and N-(4-pyridyl)azoles in moderate to good yields. Certain azolyl dihydropyridines revert to the parent azole on photolysis; this appears to be a steric effect.

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J. Chem. Soc., Perkin Trans. 1, 1981, 588-592
Article type
Paper

Synthetic applications of N–N linked heterocycles. Part 9. Preparation of α-(4-pyridyl)nitroalkanes and N-(4-pyridyl)azoles by regiospecific attack of nitroalkyl and azolyl anions on N-(2,6-dimethyl-4-oxopyridin-1-yl)pyridinium salts

A. R. Katritzky, J. G. Keay, D. N. Rogers, M. P. Sammes and C. W. F. Leung, J. Chem. Soc., Perkin Trans. 1, 1981, 588
DOI: 10.1039/P19810000588

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