4,9-二氢-3H-吡啶并(3,4-B)吲哚合成路线 （共 34 条）
反应条件
boron trifluoride diethyl etherate
1.) THF, -23 deg C, 5 min, 2.) THF, Et2O, -23 deg C, 4 h; Yield given. Multistep reaction;
参考文献
Kawate; Nakagawa; Yamazaki; Hirayama; Hino
Chemical and Pharmaceutical Bulletin, 1993 , vol. 41, # 2 p. 287 - 291
反应条件
1: 4,9-dihydro-3H-pyrido[3,4-b]indole With sodium hydride in N,N-dimethyl-formamide
T=-10°C; 1 h;
2: methyl 4-toluenesulfonate in N,N-dimethyl-formamide
T=-60°C; 2 h;
参考文献
Bertrand, Martial; Poissonnet, Guillaume; Theret-Bettiol, Marie-Helene; Gaspard, Christiane; Werner, Georges H.; Pfeiffer, Bruno; Renard, Pierre; Leonce, Stephane; Dodd, Robert H.
Bioorganic and Medicinal Chemistry, 2001 , vol. 9, # 8 p. 2155 - 2164
反应条件
n-butyllithium
1.) hexane, THF, -10 deg C, 2 h, 2.) 2 h; Yield given. Multistep reaction;
参考文献
Andriamialisoa; Langlois
Journal of the Chemical Society - Series Chemical Communications, 1982 , vol. No. 19, p. 1118 - 1119
反应条件
1.1: BF3*OEt2 / tetrahydrofuran / 0.17 h / -23 °C
1.2: 68 percent / tetrahydrofuran; diethyl ether / 15 h / -23 °C
2.1: 77 percent / AgOAc / CH2Cl2 / 14 h / 25 °C
3.1: 88 percent / H2 / Rh/C / methanol; acetic acid / 192 h / 25 °C
View Scheme
参考文献
Knoelker, Hans-Joachim; Agarwal, Sameer
Synlett, 2004 , # 10 p. 1767 - 1768
反应条件
1: 49 percent / AlCl3 / CH2Cl2 / 63 h
2: 48 percent / DDQ / benzene / 0.75 h / Heating
View Scheme
参考文献
Veeraraghavan, Seshardi; Popp, Frank D.
Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 909 - 915
反应条件
1: 90 percent / ethanol / 4 h / Ambient temperature
2: 86 percent / NaBH4 / ethanol / 6 h
View Scheme
参考文献
Maiti, Bhim C.; Pakrashi, Satyesh C.
Heterocycles, 1984 , vol. 22, # 9 p. 2043 - 2046
反应条件
1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 30 min; 2.) -70 deg C, 15 min ; -5 deg C , 90 min
2: 1.) LDA / 1.) THF, hexane, -70 deg C; 2.) THF, hexane, -70 deg C, 10 min
3: 89 percent / KOH / dioxane; H2O / 24 h / Heating
4: 91 percent / iodine / methanol / 12 h / Heating
View Scheme
参考文献
Repke, David B.; Jahangir; Clark, Robin D.; Nelson, Janis T.; MacLean, David B.
Tetrahedron, 1989 , vol. 45, # 9 p. 2541 - 2550
反应条件
in dichloromethane
20 h; Inert atmosphereReflux;
参考文献
Huan, Uozhen; Klin, Beata; Darras, Fouad H.; Heilmann, Joer; Decker, Michael
European Journal of Medicinal Chemistry, 2014 , vol. 81, p. 15 - 21
反应条件
1: 1.) n-BuLi / 1.) hexane, THF, -23 deg C, 20 min, 2.) hexane, THF, -23 deg C
2: diethyl ether; tetrahydrofuran / 2 h / -78 °C
View Scheme
参考文献
Kawate; Nakagawa; Yamazaki; Hirayama; Hino
Chemical and Pharmaceutical Bulletin, 1993 , vol. 41, # 2 p. 287 - 291
反应条件
boron trifluoride diethyl etherate
1.) THF, -23 deg C, 5 min, 2.) THF, Et2O, -23 deg C, 5 h; Yield given. Multistep reaction;
参考文献
Kawate; Nakagawa; Yamazaki; Hirayama; Hino
Chemical and Pharmaceutical Bulletin, 1993 , vol. 41, # 2 p. 287 - 291
