4-甲氧基苯并环丁烯-1-甲腈合成路线 （共 19 条）
反应条件
1: 99 percent / KOH / H2O; ethanol / 5 h / 100 °C 2: 1) LDA / 1) hexane, THF, 0 deg C, 30 min, 2) HMPA, -78 deg C -> 0 deg C, 1 h 3: 1) Mg / 1) diethyl ether, 2) rt, 2 h 4: BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 5: 87 percent / MnO2 / various solvent(s) / 36 h / 180 °C 6: 53 percent / DDQ / benzene / 4.7 h / Heating 7: 1) 10 M BH3*SMe2, 2) 10percent aq. NaOH, 30percent aq. H2O2 / 1) THF, 0 deg C, 1 h, 2) rt, 6 h 8: 94 percent / oxalyl chloride, DMSO, NEt3 / CH2Cl2 / -78 °C 9: 35 percent / KMnO4, MgSO4 / acetone / 2 h View Scheme
参考文献
Shishido, Kozo; Yamashita, Akitake; Hiroya, Kou; Fukumoto, Keiichiro
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , p. 469 - 475
反应条件
1: 99 percent / KOH / H2O; ethanol / 5 h / 100 °C 2: 1) LDA / 1) hexane, THF, 0 deg C, 30 min, 2) HMPA, -78 deg C -> 0 deg C, 1 h 3: 1) Mg / 1) diethyl ether, 2) rt, 2 h 4: BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 5: 87 percent / MnO2 / various solvent(s) / 36 h / 180 °C 6: 53 percent / DDQ / benzene / 4.7 h / Heating 7: 1) 10 M BH3*SMe2, 2) 10percent aq. NaOH, 30percent aq. H2O2 / 1) THF, 0 deg C, 1 h, 2) rt, 6 h 8: 94 percent / oxalyl chloride, DMSO, NEt3 / CH2Cl2 / -78 °C 9: 50 percent / KMnO4, MgSO4 / acetone / 2 h View Scheme
参考文献
Shishido, Kozo; Yamashita, Akitake; Hiroya, Kou; Fukumoto, Keiichiro
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , p. 469 - 475
反应条件
1: 99 percent / KOH / H2O; ethanol / 5 h / 100 °C 2: 1) LDA / 1) hexane, THF, 0 deg C, 30 min, 2) HMPA, -78 deg C -> 0 deg C, 1 h 3: 1) Mg / 1) diethyl ether, 2) rt, 2 h 4: BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 5: 87 percent / MnO2 / various solvent(s) / 36 h / 180 °C 6: 53 percent / DDQ / benzene / 4.7 h / Heating View Scheme
参考文献
Shishido, Kozo; Yamashita, Akitake; Hiroya, Kou; Fukumoto, Keiichiro
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , p. 469 - 475
反应条件
1: 99 percent / KOH / H2O; ethanol / 5 h / 100 °C 2: 1) LDA / 1) hexane, THF, 0 deg C, 30 min, 2) HMPA, -78 deg C -> 0 deg C, 1 h 3: 1) Mg / 1) diethyl ether, 2) rt, 2 h 4: BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 5: 66 percent / MnO2 / various solvent(s) / 20 h / 180 °C / other dihydrobenzocyclobutenes View Scheme
参考文献
Shishido, Kozo; Yamashita, Akitake; Hiroya, Kou; Fukumoto, Keiichiro
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990 , p. 469 - 475
反应条件
sodium amide in tetrahydrofuran
T=-78 - -33°C;
参考文献
Yamashita, Shuji; Iso, Kentaro; Kitajima, Kazuki; Himuro, Masafumi; Hirama, Masahiro
Journal of Organic Chemistry, 2011 , vol. 76, # 8 p. 2408 - 2425
反应条件
1: N,N-dimethyl-acetamide / Heating
2: 64 percent / Na / liquid ammonia / -33 °C
View Scheme
参考文献
Trehan, I. R.; Singh, N. P.; Jain, Vinay K.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 6 p. 484 - 486
反应条件
in dimethyl sulfoxide
参考文献
Schiess, Peter; Rutschmann, Suzanne; Toan, Van Vien
Tetrahedron Letters, 1982 , vol. 23, # 36 p. 3669 - 3672
反应条件
1: ammonium acetate, pyridine
2: NaBH4, alkaline medium
3: N,N-dimethyl-acetamide / Heating
4: 64 percent / Na / liquid ammonia / -33 °C
View Scheme
参考文献
Trehan, I. R.; Singh, N. P.; Jain, Vinay K.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 6 p. 484 - 486
反应条件
1: NaBH4, alkaline medium
2: N,N-dimethyl-acetamide / Heating
3: 64 percent / Na / liquid ammonia / -33 °C
View Scheme
参考文献
Trehan, I. R.; Singh, N. P.; Jain, Vinay K.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 6 p. 484 - 486
反应条件
1: Br2, AcONa / CHCl3
2: ammonium acetate, pyridine
3: NaBH4, alkaline medium
4: N,N-dimethyl-acetamide / Heating
5: 64 percent / Na / liquid ammonia / -33 °C
View Scheme
参考文献
Trehan, I. R.; Singh, N. P.; Jain, Vinay K.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 6 p. 484 - 486
