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Methylamination of Some 3-Nitro-1,8-naphthyridines with Liquid Methylamine/Potassium Permanganate

✍ Scribed by Woźniak, Marian ;Grzego??ek, Maria ;Surylo, Piotr

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
549 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

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.

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