Abstract
Abstract3‐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 1H‐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.
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