Premium
Methylamination of Some 3‐Nitro‐1,8‐naphthyridines with Liquid Methylamine/Potassium Permanganate
Author(s) -
Woźniak Marian,
Grzegoz̊ek Maria,
Surylo Piotr
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971227
Subject(s) - chemistry , potassium permanganate , methylamine , adduct , nitro , reagent , potassium , medicinal chemistry , permanganate , computational chemistry , organic chemistry , alkyl
3‐Nitro‐1,8‐naphthyridines ( 1a–1h ) are aminated, with a liquid methylamine solution of potassium permanganate (LMA/PP), to the corresponding 4‐methylamino‐substituted nitro compounds ( 3a–g ). The intermediary 4‐methylamino‐σ‐adducts of some 3‐nitro‐1,8‐naphthyridines are detected by 1 H‐NMR spectroscopy. Quantum chemical calculations show the reactions to be controlled by the interaction of the frontal molecular orbitals (FMO) of the reagents. Moreover, the heats of formation of the intermediary methylamino‐σ‐adducts of 1a and 1c–1h and transition states are calculated for the reactions studied. The agreement, between the calculated and observed results, is satisfactory for the reactions described.