(9CI)-三环[4.2.2.01,6]癸-2,4,9-三烯-7-胺合成路线 (共 11 条)
反应条件
1: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
2: 18 h / Heating
3: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: Ph2C=O / Irradiation
2: LiAlH4
3: p-TsOH
4: Na/NH3
5: 60percent aq. AcOH
6: pyridine
7: 1.) MeSCH2S(O)Me, 2.) BuLi, 3.) H2SO4
8: C5H5NHBr3, pyridine / CH2Cl2
9: LiCl, Li2CO3, HMPA
10: EtONa / benzene
11: p-TsN3, triethylamine / diethyl ether
12: Irradiation
13: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
14: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
15: 18 h / Heating
16: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: EtONa / benzene
2: p-TsN3, triethylamine / diethyl ether
3: Irradiation
4: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
5: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
6: 18 h / Heating
7: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: C5H5NHBr3, pyridine / CH2Cl2
2: LiCl, Li2CO3, HMPA
3: EtONa / benzene
4: p-TsN3, triethylamine / diethyl ether
5: Irradiation
6: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
7: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
8: 18 h / Heating
9: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: 86 percent / triethylamine / methanol / 24 h / Irradiation
2: pyridine, pyridinium bromide perbromide / CH2Cl2 / 3.5 h / 0 °C
3: LiCl, Li2CO3, HMPA / 42 h / 40 - 100 °C
4: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
5: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
6: 18 h / Heating
7: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: LiCl, Li2CO3, HMPA
2: EtONa / benzene
3: p-TsN3, triethylamine / diethyl ether
4: Irradiation
5: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
6: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
7: 18 h / Heating
8: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: Na/NH3
2: 60percent aq. AcOH
3: pyridine
4: 1.) MeSCH2S(O)Me, 2.) BuLi, 3.) H2SO4
5: C5H5NHBr3, pyridine / CH2Cl2
6: LiCl, Li2CO3, HMPA
7: EtONa / benzene
8: p-TsN3, triethylamine / diethyl ether
9: Irradiation
10: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
11: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
12: 18 h / Heating
13: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: LiAlH4
2: p-TsOH
3: Na/NH3
4: 60percent aq. AcOH
5: pyridine
6: 1.) MeSCH2S(O)Me, 2.) BuLi, 3.) H2SO4
7: C5H5NHBr3, pyridine / CH2Cl2
8: LiCl, Li2CO3, HMPA
9: EtONa / benzene
10: p-TsN3, triethylamine / diethyl ether
11: Irradiation
12: 100 percent / 5percent aq. NaOH / methanol / 6 h / 12 °C
13: triethylamine, (PhO)2P(O)N3 / benzene / 20 h / Heating
14: 18 h / Heating
15: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
sodium hydroxide; sodium hydrogencarbonate; dimethyl sulfate
1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h; Multistep reaction;
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813
反应条件
1: 18 h / Heating
2: 1.) NaHCO3, Me2SO4, 2.) NaOH / 1.) MeOH, 35 deg C, 40 h, 2.) MeOH, H2O, 40 deg C, 2 h
View Scheme
参考文献
Tsuji, Takashi; Nishida, Shinya; Okuyama, Masahiro; Osawa, Eiji
Journal of the American Chemical Society, 1995 , vol. 117, # 39 p. 9804 - 9813