Chemical Name: 8-Methyl-2,3,3a,4,5,6-hexahydro-1H-pyrazino[3,2,1-jk]carbazole hydrochloride
项目整合开发状态: Not Determined
项目研究机构:
合成路线: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.
📄 详细内容
合成路线: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.
参考文献标题:New antidepressive preparation pyrozindole
文献作者:Mashkovskii,M.D.; et al.
参考来源:Khim Farm Zh 1974,8(3),60-63
合成路线: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.
参考文献标题:Synhtesis of 1,10-trimethylenepyrazino[1,2-a]indoles
文献作者:Shvedov,V.I.; et al.
参考来源:Khim Farm Zh 1967,1(3),25-30
合成路线: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.
参考文献标题:Pirlindole
文献作者:Blancafort,P.; Casta馿r,J.; Thorpe,P.J.; Serradell,M.N.
参考来源:Drugs Fut 1980,5(1),39