4,5-二氧代-4,5-二氢-1H-吡咯[2,3-f]喹啉-2,7,9-三羧酸三甲酯合成路线 (共 37 条)
反应条件
1: 80 percent / manganese (IV) oxide / CHCl3; methanol / 20 h / Ambient temperature
2: 73 percent / NaOMe / methanol / 2 h / -15 °C
3: 87 percent / xylene / 4 h / Heating
4: 85 percent / HCl / methanol / 6 h / Heating
5: 2.) HCl / 1.) CH2Cl2, room temp., 12 h; 2.) 12 h, ether
6: 1.) BBr3; 2.) MeOH, H2SO4 (96percent) / 1.) CH2Cl2, room temp., 140 h; 2.) reflux, 48 h
7: 93 percent / benzoyl t-butyl nitroxide / methanol; CHCl3 / 16 h / Ambient temperature
View Scheme
参考文献
MacKenzie, A. Roderick; Moody, Christopher J.; Rees, Charles W.
Tetrahedron, 1986 , vol. 42, # 12 p. 3259 - 3268
反应条件
1: 94 percent / ethanol / 3.5 h / 45 °C
2: 97 percent / potassium carbonate / acetone / 8 h / Heating
3: 98 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
4: 80 percent / manganese (IV) oxide / CHCl3; methanol / 20 h / Ambient temperature
5: 73 percent / NaOMe / methanol / 2 h / -15 °C
6: 87 percent / xylene / 4 h / Heating
7: 85 percent / HCl / methanol / 6 h / Heating
8: 2.) HCl / 1.) CH2Cl2, room temp., 12 h; 2.) 12 h, ether
9: 1.) BBr3; 2.) MeOH, H2SO4 (96percent) / 1.) CH2Cl2, room temp., 140 h; 2.) reflux, 48 h
10: 93 percent / benzoyl t-butyl nitroxide / methanol; CHCl3 / 16 h / Ambient temperature
View Scheme
参考文献
MacKenzie, A. Roderick; Moody, Christopher J.; Rees, Charles W.
Tetrahedron, 1986 , vol. 42, # 12 p. 3259 - 3268
反应条件
1: 1) KOH / 2) KI / 1) MeOH, r.t., 5 h, 2) r.t., 2 d
2: 91 percent / hydrogen / Raney-nickel / tetrahydrofuran / 32 h / 760 Torr / Ambient temperature
3: 96 percent / 3N HCl / methanol / 4 h / Heating
4: 1) Et3N, 2) air, HCl(g) / 2) Cu(OAc)2 / 1) CH2Cl2, 30 min, 2) CH2Cl2, 4 h
5: 84 percent / hydrogen / 5percent Pd-C / tetrahydrofuran / 1.5 h / Ambient temperature
6: 81 percent / conc. HNO3 / acetic acid / 0.5 h / Ambient temperature
View Scheme
参考文献
Martin, Pierre
Helvetica Chimica Acta, 1993 , vol. 76, # 2 p. 988 - 992
反应条件
1: 84 percent / hydrogen / 5percent Pd-C / tetrahydrofuran / 1.5 h / Ambient temperature
2: 81 percent / conc. HNO3 / acetic acid / 0.5 h / Ambient temperature
View Scheme
参考文献
Martin, Pierre
Helvetica Chimica Acta, 1993 , vol. 76, # 2 p. 988 - 992
反应条件
potassium carbonate in N,N-dimethyl-formamide
T=25°C;
参考文献
Urakami, Teizi; Tanaka, Akinobu; Tanimoto, Tsuyoshi; Niki, Etsuo
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 8 p. 1493 - 1497
反应条件
1: 75 percent / LiOH, H2O / tetrahydrofuran / 5 h / Ambient temperature
2: NH4OH / H2O / 0.5 h / Ambient temperature
View Scheme
参考文献
Gainor, James A.; Weinreb, Steven M.
Journal of Organic Chemistry, 1982 , vol. 47, # 15 p. 2833 - 2837
反应条件
1: 100 percent / 0.05M Na2CO3 / H2O / 24 h / 30 °C
2: 84 percent / thiophenol / acetonitrile / 2 h
View Scheme
参考文献
Itoh, Shinobu; Ohshiro, Yoshiki; Agawa, Toshio
Bulletin of the Chemical Society of Japan, 1986 , vol. 59, # 6 p. 1911 - 1914