Ammonia → 6-Ethyl-5,6,7,8-tetrahydro-3-nitro-1,6-naphthyridine

反応式

[CH2:1]([N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].C[N:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=C([N+]([O-])=O)C1=O.N>>[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2[N:11]=[CH:16][C:15]([N+:17]([O-:19])=[O:18])=[CH:14][C:5]=2[CH2:4]1)[CH3:2]

参加物

反応物 3

HCID 222Ammonia

HCID 771591-Ethylpiperidin-4-one

HCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

生成物 1

HCID 234991596-Ethyl-5,6,7,8-tetrahydro-3-nitro-1,6-naphthyridine収率 93%

実験手順

1-Ethyl-4-piperidone (500 mg, 3.93 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone (392 mg, 1.97 mmol) in 1M methanolic ammonia (40 mL, 40 mmol) and heated at reflux for 3 h. The solvent was evaporated off and the residue was suspended in CHCl3 and flash chromatographed over silica gel (32 g) eluting with EtOAc to afford an orange solid (379 mg, 93% yield).