3- Nitro-4-methylamino-1,5-naphthyridine

Tliis methodology has also been extended to the use of liquid methylamine/ potassium permanganate (LMA/PP system). When this system is applied to a number of 3-nitro-l,8-naphthyridines (92a-92g), the C-4 position could be successfully substituted by methylamino group yielding 93a-93f. Tire intermediary 4-methylamino-[Pg.305]

As discussed before, in liquid ammonia/potassium permanganate nucleo-phugal substituents at C-2, such as ones present in the naphthyridines (84c, 84e, 84h, 84i, 841, and 84m), could not be replaced by the amino group only SnH substitution takes place. However, it has been observed that in the reaction of the 2-chloro-3-nitro-l,8-naphthyridine (92c) with liquid methylamine/potassium permanganate S H substitution as well as methylamino-dechlorination takes place, yielding 2,4-bis-(methylamino)-3-nitro-l,8-naphthyridine (93c). 

Tlie 4-methylamino-3-nitro-l,8-naphthyridines (110, R = H, NHCH3) undergo hydrolysis when heated with aqueous hydroehlorie aeid to give in... 

Tire heats of formation of the intermediate methylamino-transition states of the SnFI methylamination reaction of these nitro-1,8-naphthyridines were calculated by the PM3 method. Tire agreement between the calculated and observed results was found to be satisfactory (97LAR2601,97MI4). 

Similarly, NMR spectra of some 3-nitro-l,8-naphthyridines in liquid methylamine were measured (97LAR2601) (see Table IV). Tliey conclusively show that in this solution the covalent 4-methylamino-nitro compounds are present. 

Chloro-3-nitro- (53, R = C1) gave 2-methylamino-3-nitro-l,5-naphthyridine (53, R = NHMe) (MeNH2, MeOH, 20°C, 1 h 58%).854... 

In a similar way, 3-nitro-l,8-naphthyridine gave 4-methylamino-3-nitro-l,8-naphthyridine (14, R = H) (neat MeNH2 KMn04 90%) 682 and 3-nitro-l,8-naphthyridin-2-amine gave 4-methylamino-3-nitro-l,8-naphthyridin-2-amine... 

Methylamino-1,8-naphthyridine-3-caibonitrile 2-Methylamino-1,8-naphthyridine-3-caiboxamide Methyl 2-amino-1,8-naphthyridine-3-carboxylate 4-Methylamino-3-nitro-1,8-naphthyridin-2-amine 2-Methylamino-3-nitro-1,8-naphthyridine 4-Methylamino-3-nitro-1,8-naphthyridine 2-[Pg.402]

Amino-3-nitro-l,8-naphthyridin-5(8H)-one 4-(methylamino)-3-nitro-l,8-naphthyridin-... 

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