2,3,4,5-四氢-7-甲氧基-1H-苯并[d]氮杂卓合成路线 （共 18 条）
反应条件
1: 99 percent / 48 percent aq. HBr / 3 h / Heating 2: 93 percent / Et3N / tetrahydrofuran; H2O / 18 h / 20 °C 3: 92 percent / Et3N / CH2Cl2 / 18 h / -20 °C 4: 97 percent / Pd(PPh3)4 / dimethylformamide / 4 h / 100 °C 5: 100 percent / TFA / CH2Cl2 / 4 h / 20 °C View Scheme
参考文献
Austin, Nigel E.; Avenell, Kim Y.; Boyfield, Izzy; Branch, Clive L.; Hadley, Michael S.; Jeffrey, Phillip; Johnson, Christopher N.; Macdonald, Gregor J.; Nash, David J.; Riley, Graham J.; Smith, Alexander B.; Stemp, Geoffrey; Thewlis, Kevin M.; Vong, Antonio K. K.; Wood, Martyn
Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 22 p. 2553 - 2555
反应条件
1: With borane-THF in tetrahydrofuran
T=0°C; 3 h; Heating / reflux;
2: With methanol in tetrahydrofuran
T=0 - 20°C; 0.583333 h;
3: With hydrogenchloride; sodium hydroxide
more than 3 stages;
参考文献
Kuo, Gee-Hong; Zhang, Yan; Shen, Lan; Lu, Songfeng; Demarest, Keith T.; Peiton, Patricia
Patent: US2007/244094 A1, 2007 ;
Location in patent: Page/Page column 30-31 ;
反应条件
sodium in ammonia
0.5 h;
参考文献
Kanao; Hashizume; Ichikawa; Irie; Satoh; Isoda
Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 180 - 188
反应条件
N-ethyl-N,N-diisopropylamine in 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran
参考文献
Renhowe, Paul A.; Chu, Daniel; Boyce, Rustum S.; Ni, Zhi-Jie; Duhl, David; Tozzo, Effie; Johnson, Kirk; Myles, David C.
Patent: US2002/137939 A1, 2002 ;
反应条件
1: K2CO3 / acetone / 20 h / Heating
2: NaOH / ethanol; H2O / 5 h / Heating
3: SOCl2 / benzene / 8 h / Heating
4: 42 percent / AlCl3 / CH2Cl2 / 1.) 5 h, -65 deg C, 2.) 12 h, room temp.
5: 68 percent / NaBH4 / methanol / 1.) 1 h, room temp., 2.) 0.5 h, reflux
6: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating
7: 92 percent / H2 / PtO2 / acetic acid
8: 92 percent / Na / liquid ammonia / 0.5 h
View Scheme
参考文献
Kanao; Hashizume; Ichikawa; Irie; Satoh; Isoda
Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 180 - 188
反应条件
1: 92 percent / H2 / PtO2 / acetic acid
2: 92 percent / Na / liquid ammonia / 0.5 h
View Scheme
参考文献
Kanao; Hashizume; Ichikawa; Irie; Satoh; Isoda
Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 180 - 188
反应条件
1: 68 percent / NaBH4 / methanol / 1.) 1 h, room temp., 2.) 0.5 h, reflux
2: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating
3: 92 percent / H2 / PtO2 / acetic acid
4: 92 percent / Na / liquid ammonia / 0.5 h
View Scheme
参考文献
Kanao; Hashizume; Ichikawa; Irie; Satoh; Isoda
Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 180 - 188
反应条件
1: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating
2: 92 percent / H2 / PtO2 / acetic acid
3: 92 percent / Na / liquid ammonia / 0.5 h
View Scheme
参考文献
Kanao; Hashizume; Ichikawa; Irie; Satoh; Isoda
Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 180 - 188
反应条件
1: SOCl2 / benzene / 8 h / Heating
2: 42 percent / AlCl3 / CH2Cl2 / 1.) 5 h, -65 deg C, 2.) 12 h, room temp.
3: 68 percent / NaBH4 / methanol / 1.) 1 h, room temp., 2.) 0.5 h, reflux
4: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating
5: 92 percent / H2 / PtO2 / acetic acid
6: 92 percent / Na / liquid ammonia / 0.5 h
View Scheme
参考文献
Kanao; Hashizume; Ichikawa; Irie; Satoh; Isoda
Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 1 p. 180 - 188
反应条件
Pd(OH)2/C; ammonium formate in methanol
Reflux;
参考文献
Shah, Unmesh; Lankin, Claire M.; Boyle, Craig D.; Chackalamannil, Samuel; Greenlee, William J.; Neustadt, Bernard R.; Cohen-Williams, Mary E.; Higgins, Guy A.; Ng, Kwokei; Varty, Geoffrey B.; Zhang, Hongtao; Lachowicz, Jean E.
Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 14 p. 4204 - 4209
