合成路线1

The nitrosation of p-anisidine (I) with NaNO2 and HCl in water gives 4-methoxyphenyldiazonium chloride (II), which is condensed with 4-(4-methyl-1-cyclohexenyl)morpholine (III) yielding 2-(4-methoxyphenylhydrazono)-4-methylcyclohexanone (IV). The cyclization of (IV) by means of H2SO4 in refluxing ethanol affords 6-methoxy-4-methyl-1,2,3,4-tetrahydro-9H-carbazol-1-one (V), which is condensed with refluxing ethyl formate and NaH to give the corresponding 2-(hydroxymethylene) derivative (VI). The alkylation of (VI) with isopropyl iodide and K2CO3 yields the corresponding 2-(isopropoxymethylene) derivative (VII), which is methylated with CH3Li in ether to afford 6-methoxy-1,4-dimethyl-3,4-dihydrocarbazole-2-carboxaldehyde (VIII). The aromatization of (VIII) with MnO2 in refluxing benzene gives the corresponding carbazole (IX), which is condensed with malonic acid by means of piperidine in refluxing pyridine to afford 3-(6-methoxy-1,4-dimethylcarbazol-2-yl)-2-propenoic acid (X). The reaction of (X) with ethylchloroformate and sodium azide and acetone gives the corresponding azide (XI), which is cyclized by means of tributylamine in diphenyl ether at 250 C yielding 9-methoxy-5,11-dimethyl-1,2-dihydro-6H-pyrido[4,3-b]carbazol-1-one (XII). The reaction of (XII) with refluxing POCl3 affords 1-chloro-9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole (XIII), which is finally treated with refluxing 2-(diethylamino)propylamine (XIV).