6-(氨基羰基)-3,6,7,8-四氢-5-羟基-4-甲氧基苯并[1,2-b:4,3-b]二吡咯-2-羧酸合成路线 （共 22 条）
反应条件
1: 85 percent / anhydrous HCl / methanol / 12 h / 70 °C
2: 76 percent / tetrahydrofuran / 0.33 h / 22 °C
3: 81 percent / 1.) H2O2, BF3*Et2O / 3.) DMAP / 1.) CH2Cl2; 2.) CH2Cl2, 8 min, 23 deg C; 3.) CH2Cl2, 23 deg C, 18 h
4: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C
View Scheme
参考文献
Boger,D.L.; Coleman,R.S.
Journal of the American Chemical Society, 1987 , vol. 109, p. 2717
反应条件
1: 81 percent / DMAP / CH2Cl2 / 18 h / 23 °C
2: 96 percent / LiOH / tetrahydrofuran; methanol; H2O / 1 h / 50 °C
View Scheme
参考文献
Boger,D.L.; Coleman,R.S.
Journal of the American Chemical Society, 1987 , vol. 109, p. 2717
反应条件
1: Et3SiH-trifluoroacetic acid / CH2Cl2 / 0 - 20 °C
2: acetic acid
3: 68 percent / MeC(CH2OH)3, KOH / methanol
4: 75 percent / 0.01 M aq. KOH / aq. KOH
View Scheme
参考文献
Carter; Fitzjohn; Magnus
Journal of the Chemical Society - Series Chemical Communications, 1986 , vol. No. 15, p. 1162 - 1164
反应条件
1: acetic acid
2: 68 percent / MeC(CH2OH)3, KOH / methanol
3: 75 percent / 0.01 M aq. KOH / aq. KOH
View Scheme
参考文献
Carter; Fitzjohn; Magnus
Journal of the Chemical Society - Series Chemical Communications, 1986 , vol. No. 15, p. 1162 - 1164
反应条件
1: 68 percent / MeC(CH2OH)3, KOH / methanol
2: 75 percent / 0.01 M aq. KOH / aq. KOH
View Scheme
参考文献
Carter; Fitzjohn; Magnus
Journal of the Chemical Society - Series Chemical Communications, 1986 , vol. No. 15, p. 1162 - 1164
反应条件
1: benzene / Ambient temperature
2: H2 / Pd-C / methanol / 3040 Torr
View Scheme
参考文献
Bolton, Richard E.; Moody, Christopher J.; Rees, Charles W.; Tojo, Gabriel
Journal of the Chemical Society, Chemical Communications, 1985 , # 24 p. 1775 - 1776
反应条件
1: NaBH3CN, AcOH / Ambient temperature
2: benzene / Ambient temperature
3: H2 / Pd-C / methanol / 3040 Torr
View Scheme
参考文献
Bolton, Richard E.; Moody, Christopher J.; Rees, Charles W.; Tojo, Gabriel
Journal of the Chemical Society, Chemical Communications, 1985 , # 24 p. 1775 - 1776
反应条件
1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / |Inert atmosphere
2: copper(l) iodide; caesium acetate; caesium carbonate / dimethyl sulfoxide / 3 h / 90 °C / |Inert atmosphere; |Glovebox
3: thiophenol / acetonitrile / 4 h / 20 °C / |Inert atmosphere
4: sodium cyanoborohydride / acetic acid / 1 h / 20 °C / |Inert atmosphere
5: 4-(N,N-dimethlyamino)pyridine / acetic acid; dichloromethane / 5 h / 20 °C / |Inert atmosphere
6: boron trichloride / dichloromethane / 22 h / 0 - 20 °C / |Inert atmosphere
7: sodium dithionite; lithium hydroxide hydrate / water; tetrahydrofuran / 9 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Okano, Kentaro; Mitsuhashi, Nakako; Tokuyama, Hidetoshi
Tetrahedron, 2013 , vol. 69, # 51 p. 10946 - 10954
反应条件
1: sodium cyanoborohydride / acetic acid / 1 h / 20 °C / |Inert atmosphere
2: 4-(N,N-dimethlyamino)pyridine / acetic acid; dichloromethane / 5 h / 20 °C / |Inert atmosphere
3: boron trichloride / dichloromethane / 22 h / 0 - 20 °C / |Inert atmosphere
4: sodium dithionite; lithium hydroxide hydrate / water; tetrahydrofuran / 9 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Okano, Kentaro; Mitsuhashi, Nakako; Tokuyama, Hidetoshi
Tetrahedron, 2013 , vol. 69, # 51 p. 10946 - 10954
反应条件
1: 4-(N,N-dimethlyamino)pyridine / acetic acid; dichloromethane / 5 h / 20 °C / |Inert atmosphere
2: boron trichloride / dichloromethane / 22 h / 0 - 20 °C / |Inert atmosphere
3: sodium dithionite; lithium hydroxide hydrate / water; tetrahydrofuran / 9 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Okano, Kentaro; Mitsuhashi, Nakako; Tokuyama, Hidetoshi
Tetrahedron, 2013 , vol. 69, # 51 p. 10946 - 10954
