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Oxidative Methylamination of Nitroquinolines
Author(s) -
Woźniak Marian,
Grzegożek Maria
Publication year - 1993
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.1993199301130
Subject(s) - chemistry , potassium permanganate , regioselectivity , adduct , quinoline , methylamine , reagent , nitration , medicinal chemistry , quantum chemical , oxidative phosphorylation , nuclear magnetic resonance spectroscopy , potassium , stereochemistry , organic chemistry , molecule , biochemistry , catalysis
3‐, 5‐, 6‐, 7‐ and 8‐nitroquinoline as well as 5,7‐ and 6,8‐dinitroquinoline are methylaminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono‐ and bis(methylamino)‐substituted compounds. 2‐Nitroquinoline is aminated with LMA/PP to 2‐(methylamino)quinoline. The intermediate methylamino σ‐adducts of 3‐nitro‐ and 5,7‐ and 6,8‐dinitroquinoline are detected by 1 H‐NMR spectroscopy. Quantum chemical calculations for the mononitroquinolines suggest that the experimentally observed regioselectivity of the methylamination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents.