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Amination of Some Nitroisoquinolines with Liquid Methylamine/Potassium Permanganate

✍ Scribed by Woźniak, Marian ;Nowak, Krystyna

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
631 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

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(methylamino)‐substituted nitro compounds 2 (a–m). 1‐Nitroisoquinoline (1g) is aminated with LMA/PP to 1‐(methylamino)isoquinoline (2n). Quantum‐chemical calculations for some mononitroisoquinolines suggest that, in general, the experimentally observed regioselectivity of the amination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents. magnified image

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