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Amination of Some Nitroisoquinolines with Liquid Methylamine/Potassium Permanganate
Author(s) -
Woźniak Marian,
Nowak Krystyna
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940407
Subject(s) - chemistry , methylamine , potassium permanganate , amination , reagent , nitro , isoquinoline , regioselectivity , medicinal chemistry , electrophilic amination , potassium , organic chemistry , catalysis , alkyl
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.