3,4-二氢-2(1H)-喹啉酮合成路线 （共 181 条）
反应条件
1.1: 80 percent / CuI; trans-cyclohexane-1,3-diamine; K2CO3 / dioxane / 125 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C
2.2: tetrahydrofuran
View Scheme
参考文献
Beadle, Christopher D.; Boot, John; Camp, Nicholas P.; Dezutter, Nancy; Findlay, Jeremy; Hayhurst, Lorna; Masters, John J.; Penariol, Roberta; Walter, Magnus W.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4432 - 4437
反应条件
1.1: 80 percent / CuI; trans-cyclohexane-1,3-diamine; K2CO3 / dioxane / 125 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C
2.2: tetrahydrofuran / -78 - 20 °C
View Scheme
参考文献
Beadle, Christopher D.; Boot, John; Camp, Nicholas P.; Dezutter, Nancy; Findlay, Jeremy; Hayhurst, Lorna; Masters, John J.; Penariol, Roberta; Walter, Magnus W.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4432 - 4437
反应条件
1.1: 80 percent / CuI; trans-cyclohexane-1,3-diamine; K2CO3 / dioxane / 125 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C
2.2: tetrahydrofuran / -78 - 20 °C
View Scheme
参考文献
Beadle, Christopher D.; Boot, John; Camp, Nicholas P.; Dezutter, Nancy; Findlay, Jeremy; Hayhurst, Lorna; Masters, John J.; Penariol, Roberta; Walter, Magnus W.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4432 - 4437
反应条件
1: With potassium carbonate; trans-1,2diaminocyclohexane in 1,4-dioxane
T=125°C; 0.0833333 h; Heating / reflux;
2: With copper(l) iodide in 1,4-dioxane
T=125°C; Heating / reflux;
参考文献
ELI LILLY AND COMPANY
Patent: WO2005/20976 A2, 2005 ;
Location in patent: Page/Page column 206 ;
WO 2005/020976 A2
反应条件
1.1: 80 percent / CuI; trans-cyclohexane-1,3-diamine; K2CO3 / dioxane / 125 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C
2.2: tetrahydrofuran
View Scheme
参考文献
Beadle, Christopher D.; Boot, John; Camp, Nicholas P.; Dezutter, Nancy; Findlay, Jeremy; Hayhurst, Lorna; Masters, John J.; Penariol, Roberta; Walter, Magnus W.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4432 - 4437
反应条件
sodium hydride in N,N-dimethyl-formamide; mineral oil
T=0 - 20°C; Inert atmosphere;
参考文献
Winter, Dana K.; Drouin, Alexandre; Lessard, Jean; Spino, Claude
Journal of Organic Chemistry, 2010 , vol. 75, # 8 p. 2610 - 2618
反应条件
1.1: 85 percent / NaH / dimethylformamide / 10 - 20 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.5 h / -78 °C
2.2: 100 percent / tetrahydrofuran
View Scheme
参考文献
Beadle, Christopher D.; Boot, John; Camp, Nicholas P.; Dezutter, Nancy; Findlay, Jeremy; Hayhurst, Lorna; Masters, John J.; Penariol, Roberta; Walter, Magnus W.
Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4432 - 4437
反应条件
1: 1.) LDA / 1.) THF, hexane, RT, 1.75 h, 2.) THF, hexane, from -78 deg C to RT, overnight
2: 1.) LDA / 1.) THF, hexane, RT, 1.75 h, 2.) THF, hexane, from -78 deg C to RT, overnight
View Scheme
参考文献
Robertson; Krushinski; Beedle; Wyss; Pollock; Wilson; Kauffman; Hayes
Journal of Medicinal Chemistry, 1986 , vol. 29, # 10 p. 1832 - 1840
反应条件
1: 69 percent / N-bromosuccinimide / dimethylformamide / 0.25 h / 100 °C
2: 71 percent / n-Bu4NBr, KOH, (Ph3P)4Pd / tetrahydrofuran / 48 h / Heating
View Scheme
参考文献
MERCK SHARP and DOHME CORP.; ElexoPharm GmbH; HOYT, Scott, B.; PETRILLI, Whitney Lane; LONDON, Clare; XIONG, Yusheng; TAYLOR, Jerry Andrew; ALI, Amjad; LO, Michael; HENDERSON, Timothy, J.; HU, Qingzhong; HARTMANN, Rolf; YIN, Lina; HEIM, Ralf; BEY, Emmanuel; SAXENA, Rohit; SAMANTA, Swapan Kumar; KULKARNI, Bheemashankar, A.
Patent: WO2012/148808 A1, 2012 ;
WO 2012/148808 A1
反应条件
1.1: lithium diisopropylamide / tetrahydrofuran / 1.5 h / -78 - 20 °C
1.2: 61 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C
2.1: 50 percent / HNO3; H2SO4 / H2O / 0.08 h / 0 °C
3.1: 75 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; phosphorus oxychloride / dimethylformamide / 2 h / 20 °C
View Scheme
参考文献
Lee, Byoung Se; Chu, Soyoung; Lee, Kyo Chul; Lee, Bon-Su; Chi, Dae Yoon; Choe, Yearn Seong; Kim, Sang Eun; Song, Yun Seon; Jin, Changbae
Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 23 p. 4949 - 4958
