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Methylamination of some 3-nitro-1,5-naphthyridines with liquid methylamine/potassium permanganate

✍ Scribed by Maria Grzegożek; Barbara Szpakiewicz

Publisher
Journal of Heterocyclic Chemistry
Year
2006
Tongue
English
Weight
373 KB
Volume
43
Category
Article
ISSN
0022-152X

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✦ Synopsis

1,5-naphthyridine and its 2-substituted derivatives (1a-f) are dehydro-methylaminated with a solution of potassium permanganate in liquid methylamine (LMA-PP) to the corresponding 4methylamino-3-nitro-1,5-naphthyridines (3a-e). The intermediary 4-methylamino adducts of 2-R-3-nitro-1,5-naphthyridines (R = H, NH 2 , Cl, NHCH 3 , OC 2 H 5 , OH) (2a-f) are detected by 1 H nmr spectroscopy. The observed highly regioselective course of study reactions was confirmed by PM3 quantum chemical calculations of the reaction pathway. The calculations show satisfactory agreement between calculated and observed results. A convenient synthesis of 2-hydroxy-and 4-methylamino-3-nitro-1,5-naphthyridine are reported.

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