3,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮合成路线 （共 36 条）
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 51 percent / cerium ammonium nitrate
3: 24 percent / electrochemical oxidation
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C
2: 93 percent / HCl / diethyl ether / 65 h / Heating
3: 86 percent / NiCl2, BaBH4 / methanol / 0.08 h / 50 °C
4: 64 percent / aq. HCl / tetrahydrofuran / 1 h / 40 °C
5: 51 percent / cerium ammonium nitrate
7: 24 percent / electrochemical oxidation
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 1.) AcOH, FeCl3, 2.) AcOH / 1.) 60 deg C, 5 min, 2.) reflux, 5 h
2: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min
3: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C
4: 93 percent / HCl / diethyl ether / 65 h / Heating
5: 86 percent / NiCl2, BaBH4 / methanol / 0.08 h / 50 °C
6: 64 percent / aq. HCl / tetrahydrofuran / 1 h / 40 °C
7: 51 percent / cerium ammonium nitrate
9: 24 percent / electrochemical oxidation
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
sodium methylate in methanol
Yield given;
参考文献
Aubart, Kelly Marshall; Heathcock, Clayton H.
Journal of Organic Chemistry, 1999 , vol. 64, # 1 p. 16 - 22
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH
2: CuCl2, Et3N, O2 / acetonitrile
3: NaOMe / methanol
View Scheme
参考文献
Aubart, Kelly Marshall; Heathcock, Clayton H.
Journal of Organic Chemistry, 1999 , vol. 64, # 1 p. 16 - 22
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 82 percent / Fremy's salt / acetone; H2O
2: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH
3: CuCl2, Et3N, O2 / acetonitrile
4: NaOMe / methanol
View Scheme
参考文献
Aubart, Kelly Marshall; Heathcock, Clayton H.
Journal of Organic Chemistry, 1999 , vol. 64, # 1 p. 16 - 22
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: CuCl2, Et3N, O2 / acetonitrile
2: NaOMe / methanol
View Scheme
参考文献
Aubart, Kelly Marshall; Heathcock, Clayton H.
Journal of Organic Chemistry, 1999 , vol. 64, # 1 p. 16 - 22
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 76 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C
2: 84 percent / HCl / diethyl ether / 48 h / Heating
3: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h
4: 64 percent / aq. HCl / tetrahydrofuran / 0.5 h / 40 °C
6: 24 percent / electrochemical oxidation
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 84 percent / HCl / diethyl ether / 48 h / Heating
2: 80 percent / NiCl2, NaBH4 / methanol / 0.33 h
3: 64 percent / aq. HCl / tetrahydrofuran / 0.5 h / 40 °C
5: 24 percent / electrochemical oxidation
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
→
105372-81-43,5-二溴-2',3',5',7',8',9'-六氢-螺[2,5-环己二烯-1,10'(6'H)-吡咯并[4,3,2-de][1,7]菲咯啉]-4,6'-二酮
反应条件
1: 64 percent / aq. HCl / tetrahydrofuran / 0.5 h / 40 °C
3: 24 percent / electrochemical oxidation
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
