(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮合成路线 （共 17 条）
→
109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: 86 percent / BF3*Et2O / 4 h / -25 - -18 °C 2: 100 percent / n-Bu4NF*3H2O / tetrahydrofuran / 1.5 h / -21 - -17 °C 3: 846 mg / CrO3, pyridine / CH2Cl2 / 0.5 h / Ambient temperature 4: NH3 / methanol / 20 h / Ambient temperature 5: 82 percent / TFA / H2O / 5 h / Ambient temperature View Scheme
参考文献
Chemical and Pharmaceutical Bulletin, , vol. 39, # 6 p. 1392 - 1396
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109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: 92 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 2: 86 percent / BF3*Et2O / 4 h / -25 - -18 °C 3: 100 percent / n-Bu4NF*3H2O / tetrahydrofuran / 1.5 h / -21 - -17 °C 4: 846 mg / CrO3, pyridine / CH2Cl2 / 0.5 h / Ambient temperature 5: NH3 / methanol / 20 h / Ambient temperature 6: 82 percent / TFA / H2O / 5 h / Ambient temperature View Scheme
参考文献
Chemical and Pharmaceutical Bulletin, , vol. 39, # 6 p. 1392 - 1396
→
109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: 100 percent / n-Bu4NF*3H2O / tetrahydrofuran / 1.5 h / -21 - -17 °C 2: 846 mg / CrO3, pyridine / CH2Cl2 / 0.5 h / Ambient temperature 3: NH3 / methanol / 20 h / Ambient temperature 4: 82 percent / TFA / H2O / 5 h / Ambient temperature View Scheme
参考文献
Chemical and Pharmaceutical Bulletin, , vol. 39, # 6 p. 1392 - 1396
→
109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: DCC, HOBT / dimethylformamide / Ambient temperature 2: 66 percent / imidazole / dimethylformamide / 0 °C 3: 92 percent / NaBH4 / methanol / Ambient temperature 4: 86 percent / BF3*Et2O / -20 °C 5: 100 percent / n-BuNF / tetrahydrofuran / -20 °C 6: CrO3*2Py / CH2Cl2 / Ambient temperature 7: 55 percent / NH3 / methanol / Ambient temperature 8: 82 percent / 75percent TFA-H2O / Ambient temperature View Scheme
参考文献
Tetrahedron Letters, , vol. 31, # 2 p. 225 - 226
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109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: dicyclohexylcarbodiimide, 1-hydroxybenzotriazole, Et3N / dimethylformamide / 20 h / Ambient temperature 2: imidazole / dimethylformamide / 6 h / ice-water bath 3: 92 percent / NaBH4 / methanol / 0.5 h / Ambient temperature 4: 86 percent / BF3*Et2O / 4 h / -25 - -18 °C 5: 100 percent / n-Bu4NF*3H2O / tetrahydrofuran / 1.5 h / -21 - -17 °C 6: 846 mg / CrO3, pyridine / CH2Cl2 / 0.5 h / Ambient temperature 7: NH3 / methanol / 20 h / Ambient temperature 8: 82 percent / TFA / H2O / 5 h / Ambient temperature View Scheme
参考文献
Chemical and Pharmaceutical Bulletin, , vol. 39, # 6 p. 1392 - 1396
→
109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮
反应条件
1: NH3 / methanol / 0.17 h 2: CrO3*2C5H5N / CH2Cl2 3: NH3 / methanol 4: 75percent aq. CF3COOH View Scheme
参考文献
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 10 p. 1095 - 1098
109944-15-2(5R,6R,7S,8R,8aS)-6,7,8-三羟基-5-(羟基甲基)-1,5,6,7,8,8a-六氢咪唑并[1,2-a]吡啶-2,3-二酮+
→
134234-43-8(3aS,3bR,7aR,11aS,11bR)-2,2,5,5-四甲基六氢-3bH-[1,3]二恶英并[4,5-e][1,3]二氧杂环戊并[4,5-c]咪唑并[1,2-a]吡啶-9,10-二酮
反应条件
toluene-4-sulfonic acid in N,N-dimethyl-formamide T=60°C; 12 h;
参考文献
Kayakiri; Takase; Shibata; Hashimoto; Tada; Koda
Chemical and Pharmaceutical Bulletin, 1991 , vol. 39, # 6 p. 1378 - 1381
