7,8-二氢萘并[2,3-d][1,3]二氧杂环戊烯-5(6H)-酮合成路线 (共 26 条)
反应条件
1: 97 percent / Br2 / CHCl3 / Ambient temperature 2: 97 percent / DBU / acetonitrile / 0.33 h / 40 - 45 °C 3: 1.) NaOH / 1.) DMPU, room temperature, 15 min, 2.) DMPU 4: 94 percent / NaH, DMPU / dimethylformamide / 2 h / 100 °C 5: 74 percent / aq. NaOH / methanol / Heating 6: 88 percent / tetrahydrofuran / 0.75 h / Ambient temperature 7: 1.) PPh3, Pd(OAc)2, aq. Na2CO3 / 1.) DME, room temperature, 1 h, 2.) DME, reflux 8: 1.) NaH / 1.) 30 min, room temperature, 2.) room temperature, 1.5 h 9: 91 percent / POCl3 / acetonitrile / 0.5 h / Heating View Scheme
参考文献
Geen, Graham R.; Mann, Inderjit S.; Mullane, M. Valerie; McKillop, Alexander
Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 14 p. 1647 - 1648
反应条件
1: 6,7-dihydroxy-3,4-dihydro-1(2H)-naphthalenone With cesium fluoride in N,N-dimethyl-formamide
T=20°C; deprotonation; 3 h;
2: 1,1-dibromomethane in N,N-dimethyl-formamide
T=100°C; Etherification; 2 h;
参考文献
Harayama, Takashi; Yasuda, Hirotake; Akiyama, Toshihiko; Takeuchi, Yasuo; Abe, Hitoshi
Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 6 p. 861 - 864
反应条件
polyphosphate ester
T=20°C; Cyclization; 2 h;
参考文献
Zjawiony, Jordan; Peterson, John R.
Organic Preparations and Procedures International, 1991 , vol. 23, # 2 p. 163 - 172
反应条件
hydrogen; trifluoroacetic anhydride; palladium on activated charcoal
1.) THF; 2.) ClCH2-CH2Cl; Yield given. Multistep reaction;
参考文献
Thibonnet, Jerome; Abarbri, Mohamed; Parrain, Jean-Luc; Duchene, Alain
Tetrahedron Letters, 1996 , vol. 37, # 42 p. 7507 - 7510
反应条件
boron trifluoride diethyl etherate; mercury(II) oxide in tetrahydrofuran; water
参考文献
Rigby, James H.; Kotnis, Atul; Kramer, James
Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5078 - 5088
反应条件
1: 1) 9-BBN, 2) CH3ONa / 2) dichloro<1,1'-bis(diphenylphosphino)ferrocene>palladium(II) / 1) THF, room temperature, 3 h, 2) THF, reflux, 5 h
2: 94 percent / KOH / ethanol / 2 h / Ambient temperature
3: 87 percent / polyphosphonate ester / CHCl3; diethyl ether / 5 h / Ambient temperature
View Scheme
参考文献
Esteban, Gemma; Lopez-Sanchez, Miguel A.; Martinez, Ma. Eugenia; Plumet, Joaquin
Tetrahedron, 1998 , vol. 54, # 1-2 p. 197 - 212
反应条件
1: 41 percent / NaH / tetrahydrofuran; dimethylsulfoxide / 20 h / Ambient temperature
2: 100 percent / H2 / Pd/C
3: oxalyl chloride / benzene / 2 h / Heating
4: AlCl3 / CS2 / 3 h / Heating
View Scheme
参考文献
Beugelmans, Rene; Chastanet, Jacqueline; Ginsburg, Helene; Quintero-Cortes, Leticia; Roussi, Georges
Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4933 - 4938
参考文献
Akzo Nobel N.V.
Patent: US6410592 B1, 2002 ;
US 6410592 B1
反应条件
1: hydrogen / Pd/C / tetrahydrofuran / 3 h / 20 °C / 760.21 Torr
2: 85 percent / trifluoroacetic anhydride / 1,2-dichloro-ethane / 0 - 20 °C
View Scheme
参考文献
Vercouillie, Johnny; Abarbri, Mohamed; Parrain, Jean-Luc; Duchene, Alain; Thibonnet, Jerome
Synthetic Communications, 2004 , vol. 34, # 20 p. 3751 - 3762
反应条件
aluminium trichloride in carbon disulfide
3 h; Heating; Yield given;
参考文献
Beugelmans, Rene; Chastanet, Jacqueline; Ginsburg, Helene; Quintero-Cortes, Leticia; Roussi, Georges
Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4933 - 4938