N-[(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-cyclohexan-carboxamide → 3,3a,5,6-Tetrahydro-1-cyclohexyl-3a-methyl-4-oxa-2,10b-diazafluoranthene
Reaktionsgleichung
[CH3:1][C:2]1([CH2:15][NH:16][C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=O)[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[CH2:5][CH2:4][O:3]1)=[CH:13][CH:12]=[CH:11][CH:10]=3>P(Cl)(Cl)(Cl)=O>[CH:19]1([C:17]2[N:8]3[C:7]4[C:2]([CH3:1])([O:3][CH2:4][CH2:5][C:6]=4[C:14]4[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH2:15][N:16]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1Komponenten
3
Versuchsvorschrift
A mixture of N-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-cyclohexancarboxamide(1.3 g, described in Example 6) and phosphorus oxychloride (50 ml) is refluxed for 60 minutes and evaporated. The residue is dissolved in chloroform. This solution is washed quickly with 5% sodium hydroxide, dried over magnesium sulfate, filtered and evaporated. The residue is chromatographed on silica gel using chloroform and the eluates are evaporated to give the title compound (0.70 g), nmr(CDCl3) δ0.9-2.6(multiplets), 3.23(d), 3.83(d) and 4.20(m).