(9CI)-1,3,4,5-四氢-5-甲基-吡咯并[4,3,2-de]喹啉-7,8-二酮合成路线 (共 20 条)
反应条件
1.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
4.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
5.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86
6.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere
6.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
3.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
4.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86
5.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere
5.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
2.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
3.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86
4.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere
4.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
2.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86
3.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere
3.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86
2.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere
2.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1.1: acetonitrile / 4 h / |Reflux; |Inert atmosphere
2.1: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0.33 h / 0 °C / |Inert atmosphere
3.1: triethylamine / 1,2-dichloro-ethane / 10 h / 20 °C / |Inert atmosphere
4.1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux
5.1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
7.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
8.1: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
9.1: Fremy’s salt / acetone / 0.33 h / 0 - 20 °C / pH 6.86
10.1: acetone / 0.5 h / 60 °C / |Sealed tube; |Inert atmosphere
10.2: 7 h / 70 °C / |Sealed tube; |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1: 76 percent / acetonitrile / 0.5 h / 0 °C
2: 71 percent / BBr3 / CH2Cl2 / 12 h / 0 - 25 °C
3: 86 percent / CAN / acetonitrile / 0.17 h / 0 °C
4: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C
5: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Sadanandan, E. V.; Cava, Michael P.
Tetrahedron Letters, 1993 , vol. 34, # 15 p. 2405 - 2408
反应条件
1: 86 percent / CAN / acetonitrile / 0.17 h / 0 °C
2: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C
3: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Sadanandan, E. V.; Cava, Michael P.
Tetrahedron Letters, 1993 , vol. 34, # 15 p. 2405 - 2408
反应条件
1: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C
2: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Sadanandan, E. V.; Cava, Michael P.
Tetrahedron Letters, 1993 , vol. 34, # 15 p. 2405 - 2408
反应条件
1: 71 percent / BBr3 / CH2Cl2 / 12 h / 0 - 25 °C
2: 86 percent / CAN / acetonitrile / 0.17 h / 0 °C
3: 36 percent / dithienyl ditelluride, NaBH4, NaOH / tetrahydrofuran; H2O / 6 h / 67 °C
4: 76 percent / 10percent NaOH / methanol / 0.5 h / 25 °C
View Scheme
参考文献
Sadanandan, E. V.; Cava, Michael P.
Tetrahedron Letters, 1993 , vol. 34, # 15 p. 2405 - 2408