- Amination of Some Nitroisoquinolines with Liquid Methylamine/Potassium Permanganate
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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. - Key Words: Methylaminations / Calculations, FMO / Isoquinolines / Aminations / Nitro compounds
- Wozniak, Marian,Nowak, Krystyna
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p. 355 - 360
(2007/10/02)
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- THE SYNTHESIS OF THREE ISOMERS OF THE FOOD CARCINOGEN IQ
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2-Amino-3-methyl-3H-imidazoquinoline, 2-amino-3-methyl-3H-imidazoisoquinoline and 2-amino-3-methyl-3H-imidazoisoquinoline were synthesized from 7-methoxyquinoline, 6- and 7-methoxyisoquinolines in 21-28percent overall yields.
- Ronne, Erik,Grivas, Spiros
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p. 101 - 105
(2007/10/02)
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