5-乙炔苯并[1,3]间二氧杂环戊烯合成路线 （共 27 条）
反应条件
1: 87 percent / pyridine / 1.) 0 deg C, 5 min, 2.) 23 deg C, 25 h
2: 1.) LiCl, 2,6-di-tert-butyl-4-methylphenol, 2.) pyridin, pyridinium hydrofluoride / 1.) Pd(PPH3)4 / 1.) 1,4-dioxane, reflux, 4 h, 2.) THF, 23 deg C, 16 h
View Scheme
参考文献
Echavarren,A.M.; Stille,J.K.
Journal of the American Chemical Society, 1987 , vol. 109, p. 5478
反应条件
caesium carbonate in ethanol
T=0°C;
参考文献
Kumar, Rahul; Verma, Deepti; Mobin, Shaikh M.; Namboothiri, Irishi N. N.
Organic Letters, 2012 , vol. 14, # 16 p. 4070 - 4073
反应条件
pyridine; 2,6-di-tert-butyl-4-methyl-phenol; pyridine hydrogenfluoride; lithium chloride; tetrakis(triphenylphosphine) palladium(0)
1.) 1,4-dioxane, reflux, 4 h, 2.) THF, 23 deg C, 16 h; Yield given. Multistep reaction;
参考文献
Echavarren,A.M.; Stille,J.K.
Journal of the American Chemical Society, 1987 , vol. 109, p. 5478
反应条件
1: 100 percent / CuI, Et3N / (Ph3As)2PdCl2 / 1.5 h / Ambient temperature
2: 92 percent / K2CO3 / methanol / 2 h / Ambient temperature
View Scheme
参考文献
Pearson; Postich
Journal of Organic Chemistry, 1994 , vol. 59, # 19 p. 5662 - 5671
反应条件
1: 84 percent / triphenylphosphine / CH2Cl2 / 0.17 h / 0 °C
2: 95 percent / BuLi / tetrahydrofuran / -78 deg C, 1h, then RT, 1.5 h
View Scheme
参考文献
Pelter, Andrew; Ward, Robert S.; Little, Gillian M.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , # 10 p. 2775 - 2790
反应条件
1: carbon tetrabromide With triphenylphosphine in dichloromethane
T=0°C; Corey-Fuchs homologation; 0.25 h;
2: piperonal in dichloromethane
T=0°C; Corey-Fuchs homologation; 0.55 h;
3: With n-butyllithium in tetrahydrofuran
T=-78°C; Corey-Fuchs homologation; 0.666667 h;
参考文献
Mahoney, Stuart J.; Moon, David T.; Hollinger, Jon; Fillion, Eric
Tetrahedron Letters, 2009 , vol. 50, # 33 p. 4706 - 4709
反应条件
1.1: caesium carbonate / N,N-dimethyl-formamide / 24 h / 100 °C / |Inert atmosphere; |Schlenk technique
2.1: triphenylphosphine / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere; |Schlenk technique
2.2: 2 h / 20 °C / |Inert atmosphere; |Schlenk technique
3.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / |Inert atmosphere; |Schlenk technique
View Scheme
参考文献
Xiong, Ya-Ping; Wu, Ming-Yue; Zhang, Xiang-Yu; Ma, Can-Liang; Huang, Lin; Zhao, Li-Jiao; Tan, Bin; Liu, Xin-Yuan
Organic Letters, 2014 , vol. 16, # 3 p. 1000 - 1003
反应条件
18-crown-6 ether; potassium tert-butylate in cyclohexane
2 h; Heating;
参考文献
Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.
Tetrahedron, 2006 , vol. 62, # 17 p. 4214 - 4226
反应条件
1: bromine / CH2Cl2 / 0 °C
2: 1 g / potassium t-butoxide; 18-crown-6 / cyclohexane / 2 h / Heating
View Scheme
参考文献
Aslam, Shazia N.; Stevenson, Philip C.; Phythian, Sara J.; Veitch, Nigel C.; Hall, David R.
Tetrahedron, 2006 , vol. 62, # 17 p. 4214 - 4226
反应条件
1.1: Et3N / CH2Cl2 / 0.5 h / 0 °C
2.1: 1.03 g / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH2Cl2 / 0.5 h / 20 °C
3.1: t-BuMgCl; EtMgCl / tetrahydrofuran / -78 °C
3.2: 87 percent / PhSO2C(Li)HPh; HMPA / tetrahydrofuran / -78 - 20 °C
View Scheme
参考文献
Satoh, Tsuyoshi; Sakamoto, Tatsuya; Watanabe, Masanori; Takano, Koji
Chemical and Pharmaceutical Bulletin, 2003 , vol. 51, # 8 p. 966 - 970
