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【结 构 式】 
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【分子编号】39034 【品名】9-(2,2-dibutoxyethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 【CA登记号】 |
【 分 子 式 】C23H33NO3 【 分 子 量 】371.51996 【元素组成】C 74.36% H 8.95% N 3.77% O 12.92% |
合成路线1
该中间体在本合成路线中的序号：(V)Compound can be prepared in two different ways: 1) The cyclization of 1,2-cyclohexanedione mono-p-tolylhydrazone (I) by means of formic acid in DMF gives 1,2,3,4-tetrahydro-6-methylcarbazole-1-one (II), which by condensation with chloroacetonitrile (A) by means of sodium ethoxide in dioxane is converted into 1,2,3,4-tetrahydro-6-methyl-9-cyanomethylcarbazole-1-one (III). Finally, this compound is submitted to a reductive cyclization with H2 over Raney-Ni in methanol at 30 atm. and 50 C. 2) The carbazolone (II) can also be condensed with 2-bromoacetaldehyde dibutylacetal (B) by means of sodium ethoxide to afford 1,2,3,4-tetrahydro-6-methyl-9-(beta,beta-dibutoxyethyl)carbazole-1-one (IV), which is cyclized with ammonium acetate in acetic acid yielding 1,2,5,6-tetrahydromethylpyrazino[3,2,1-j,k]-4H-carbazole (V). Finally, this compound is reduced with H2 over Pd/C.
| 【1】 Blancafort, P.; Castañer, J.; Thorpe, P.J.; Serradell, M.N.; Pirlindole. Drugs Fut 1980, 5, 1, 39. |
| 【2】 Shvedov, V.I.; et al.; Synhtesis of 1,10-trimethylenepyrazino[1,2-a]indoles. Khim Farm Zh 1967, 1, 3, 25-30. |
| 【3】 Mashkovskii, M.D.; et al.; New antidepressive preparation pyrozindole. Khim Farm Zh 1974, 8, 3, 60-63. |
| 【4】 Mashkovskii, M.D.; et al.; GB 1340528 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 14443 | 2-chloroacetonitrile; chloroacetonitrile | 107-14-2 | C2H2ClN | 详情 | 详情 |
| (I) | 39030 | 1,2-cyclohexanedione 1-[N-(4-methylphenyl)hydrazone] | C13H16N2O | 详情 | 详情 | |
| (II) | 39031 | 6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one | C13H13NO | 详情 | 详情 | |
| (III) | 39032 | 2-(6-methyl-1-oxo-1,2,3,4-tetrahydro-9H-carbazol-9-yl)acetonitrile | C15H14N2O | 详情 | 详情 | |
| (IV) | 39033 | 1-(2-bromo-1-butoxyethoxy)butane; 2-bromo-1-butoxyethyl butyl ether | C10H21BrO2 | 详情 | 详情 | |
| (V) | 39034 | 9-(2,2-dibutoxyethyl)-6-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one | C23H33NO3 | 详情 | 详情 | |
| (VI) | 39035 | 8-methyl-2,4,5,6-tetrahydro-1H-pyrazino[3,2,1-jk]carbazole | C15H16N2 | 详情 | 详情 |