ZK-91296
Chemical Name: 5-(Benzyloxy)-4-(methoxymethyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid ethyl ester; 5-(Benzyloxy)-4-(methoxymethyl)-beta-carboline-3-carboxylic acid ethyl ester
CAS No. 83910-34-3
项目整合开发状态: Phase II
项目研究机构: Ferrosan AB (Originator), Schering AG (Originator)
合成路线:This compound can be prepared by two related ways:1) The condensation of methoxyacetaldehyde (I) with isopropylamine (II) gives methoxyacetaldehyde isopropylimine (III),which is treated with 4-benzyloxyindole (IV) in acetic acid yielding 4-benzyloxy-3-(1-isopropylamino-2-ethoxyethyl)indole (V).The reaction of (V) with ethyl nitroacetate (VI) in hot toluene affords ethyl 3-(4-benzyloxyindol-3-yl)-2-nitro-5-oxahexanoate (VII),which is reduced with H2 over Raney-Ni in ethanol giving ethyl 3-(4-benzyloxyindol-3-yl)-2-amino-5-oxahexanoate (VIII).Finally,this compound is cyclized with paraformaldehyde (IX) in refluxing benzene.2) Compound (VIII) can also be cyclized with glyoxylic acid (X) yielding a mixture of the tetrahydrocarboline (XI) and the dihydrocarboline (XII),which,without separation,are decarboxylated and dehydrogenated with sulfur at 140 C.
📌 参考资料/链接：
参考文献标题:Pharmacologically active 3-substituted beta-carbolines
文献作者:Neef,G.; Eder,U.; Schmiechen,R.; Huth,A.; Rathz,D.; Seidelmonn,D.; Kehr,W.; Palenschat,D.; Braestrup,C.T.; et al.(Schering AG)
参考来源:DD 161210; EP 0054507; ES 8301984; US 4435403; US 4596808
📄 详细内容
合成路线:This compound can be prepared by two related ways:1) The condensation of methoxyacetaldehyde (I) with isopropylamine (II) gives methoxyacetaldehyde isopropylimine (III),which is treated with 4-benzyloxyindole (IV) in acetic acid yielding 4-benzyloxy-3-(1-isopropylamino-2-ethoxyethyl)indole (V).The reaction of (V) with ethyl nitroacetate (VI) in hot toluene affords ethyl 3-(4-benzyloxyindol-3-yl)-2-nitro-5-oxahexanoate (VII),which is reduced with H2 over Raney-Ni in ethanol giving ethyl 3-(4-benzyloxyindol-3-yl)-2-amino-5-oxahexanoate (VIII).Finally,this compound is cyclized with paraformaldehyde (IX) in refluxing benzene.2) Compound (VIII) can also be cyclized with glyoxylic acid (X) yielding a mixture of the tetrahydrocarboline (XI) and the dihydrocarboline (XII),which,without separation,are decarboxylated and dehydrogenated with sulfur at 140 C.
参考文献标题:ZK-91296
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(10),761
合成路线:This compound can be prepared by two related ways:1) The condensation of methoxyacetaldehyde (I) with isopropylamine (II) gives methoxyacetaldehyde isopropylimine (III),which is treated with 4-benzyloxyindole (IV) in acetic acid yielding 4-benzyloxy-3-(1-isopropylamino-2-ethoxyethyl)indole (V).The reaction of (V) with ethyl nitroacetate (VI) in hot toluene affords ethyl 3-(4-benzyloxyindol-3-yl)-2-nitro-5-oxahexanoate (VII),which is reduced with H2 over Raney-Ni in ethanol giving ethyl 3-(4-benzyloxyindol-3-yl)-2-amino-5-oxahexanoate (VIII).Finally,this compound is cyclized with paraformaldehyde (IX) in refluxing benzene.2) Compound (VIII) can also be cyclized with glyoxylic acid (X) yielding a mixture of the tetrahydrocarboline (XI) and the dihydrocarboline (XII),which,without separation,are decarboxylated and dehydrogenated with sulfur at 140 C.
参考文献标题:Synthesis of 4-sibstituted beta-carbolines
文献作者:Neef,G.; Schmiechen,R.; Huth,A.; Eder,U.; Rathz,D.; Seidelmann,D.
参考来源:Heterocycles 1983,20(7),1295-1313
产品链接: CAS No. 83910-34-3››