3,4-二氢-2(1H)-喹啉酮合成路线 （共 181 条）
反应条件
palladium
T=250 - 260°C;
参考文献
Spaeth; Galinovsky
Chemische Berichte, 1936 , vol. 69, p. 2059
反应条件
1.1: 87 percent / N-bromosuccinimide / dimethylformamide / 2 h / 0 °C
2.1: 79 percent / Lawesson's reagent / toluene / 0.75 h / Heating
3.1: 22 percent / K2CO3; 18-crown-6 / tetrahydrofuran / 3 h / 20 °C
4.1: toluene / 0.25 h / Heating
4.2: 42 percent / DBU / toluene / 0.33 h / Heating
View Scheme
参考文献
Occhiato, Ernesto G.; Ferrali, Alessandro; Menchi, Gloria; Guarna, Antonio; Danza, Giovanna; Comerci, Alessandra; Mancina, Rosa; Serio, Mario; Garotta, Gianni; Cavalli, Andrea; De Vivo, Marco; Recanatini, Maurizio
Journal of Medicinal Chemistry, 2004 , vol. 47, # 14 p. 3546 - 3560
反应条件
1: 55 percent / aq. NaClO3; HCl; AcOH / 0.33 h / 20 °C
2: POCl3; DDQ / dimethylformamide / 6 h / 20 °C
3: dimethylformamide / 80 °C
4: 4 M aq. H2SO4 / 80 °C
View Scheme
参考文献
Lee, Byoung Se; Chu, Soyoung; Lee, Byung Chul; Chi, Dae Yoon; Choe, Yearn Seong; Jeong, Kyung Ja; Jin, Changbae
Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 14 p. 1559 - 1562
反应条件
1: 2 percent / thionyl chloride / 1 h / Heating
2: dimethylsulfoxide / 0.25 h / 70 °C
3: 89 percent / NaOH / H2O; dimethylsulfoxide
4: 94 percent / aq. HCl / ethanol / 72 h / Heating
5: 94 percent / phosphoryl chloride / 1 h / Heating
View Scheme
参考文献
Nowak, Malgorzata; Pluta, Krystian; Suwinska, Kinga
New Journal of Chemistry, 2002 , vol. 26, # 9 p. 1216 - 1220
反应条件
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / |Inert atmosphere
2.1: sodium hydroxide / tetrahydrofuran / 20 °C
2.2: pH 1
View Scheme
参考文献
ACTELION PHARMACEUTICALS LTD; CAROFF, Eva; KELLER, Marcel; KIMMERLIN, Thierry; MEYER, Emmanuel
Patent: WO2013/114332 A1, 2013 ;
反应条件
sodium hydride in tetrahydrofuran
T=20°C;
参考文献
Kobayashi, Kazuhiro; Fuchimoto, Yuhei; Hayashi, Kazutaka; Mano, Masaaki; Tanmatsu, Miyuki; Morikawa, Osamu; Konishi, Hisatoshi
Synthesis, 2005 , # 16 art. no. F05805SS, p. 2673 - 2676
反应条件
sodium hydride in tetrahydrofuran; N,N-dimethyl-formamide
参考文献
Ohbayashi, Tohru; Mitsunaga, Shintaro; Satoh, Tsuyoshi
Tetrahedron Letters, 2007 , vol. 48, # 44 p. 7829 - 7833
反应条件
potassium tert-butylate
DMF, 1.) room temp., 15 min, 2.) room temp., overnight; Yield given. Multistep reaction;
参考文献
Spaeth
Monatshefte fuer Chemie, 1919 , vol. 40, p. 31
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
3.1: ethanol; H2O / 3 h / 100 °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
3.1: ethanol; H2O / 3 h / 100 °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
