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Regioselectivity of the amination of some 3-nitropyridines by liquid ammonia/potassium permanganate

✍ Scribed by Woźniak, Marian ;Barański, Andrzej ;Szpakiewicz, Barbara


Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
424 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

3‐Nitropyridine and some of its derivatives are aminated in a liquid ammonia solution of potassium permanganate to the corresponding 2‐ and (or) 4‐ and (or) 6‐amino compounds. Quantumchemical calculations for a few 3‐nitropyridines suggest that the experimentally observed regioselectivity of the amination is controlled by Coulombic interaction.


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## Abstract 5‐Nitro‐, 3‐methyl‐5‐nitro‐, 5, 7‐dinitro‐, 5‐chloro‐8‐nitro‐ and 8‐chloro‐5‐nitroisoquinoline (1a–e) as well as 5‐nitroisoquinoline __N__‐oxide (1f) are aminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono‐ or mono‐ and bis(methylamin