1-(2-脱氧-beta-D-赤式-呋喃戊糖基)-1H-咪唑并[4,5-c]吡啶-4-胺合成路线 (共 27 条)
反应条件
1: 68 percent / KOH / tris<2-(2-methoxyethoxy)ethyl>amin (TDA-1) / acetonitrile / 0.25 h / Ambient temperature
2: 83 percent / 3-chloroperbenzoic acid (70percent) / methanol / 0.5 h / Ambient temperature
3: 85 percent / NH3, MeOH / 20 h / Ambient temperature
4: 47 percent / 25percent aq. NH3, 30percent H2O2 / 24 h / 60 °C
View Scheme
参考文献
Seela, Frank; Grein, Thomas; Samnick, Samuel
Helvetica Chimica Acta, 1992 , vol. 75, # 5 p. 1639 - 1650
反应条件
1: 1.) KOH, tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1) / 1.) MeCN, 40 deg C, 2.) 40 deg C, 15 min.
2: 86 percent / NH3/MeOH / 48 h / Ambient temperature
3: 1.) hydrazine, 2.) Raney-Ni / 1.) 90 deg C, 1 h, 2.) EtOH, reflux, 1 h
View Scheme
参考文献
Seela; Rosemeyer; Fischer
Helvetica Chimica Acta, 1990 , vol. 73, # 6 p. 1602 - 1611
反应条件
1: 84 percent / NaH / tetrahydrofuran
2: 28 percent / NaOH / ethanol / Heating
3: pyridine / 24 h / Ambient temperature
4: K2CO3, 18-crown-6-ether / dimethylformamide / 36 h / 40 °C
5: 5N NaOH / ethanol / 0.83 h / Heating
6: TFA / CH2Cl2 / 3 h / Ambient temperature
7: 98 percent / imidazole / dimethylformamide / 14 h / Ambient temperature
8: 97 percent / p-toluenesulfonyl chloride, pyridine / 24 h / Heating
9: 55 percent / isoamyl nitrite, CH2I2 / 0.33 h / 100 °C
10: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
11: NH3 / methanol
12: 70 percent / NH3 / methanol / 12 h / 120 °C
13: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: pyridine / 24 h / Ambient temperature
2: K2CO3, 18-crown-6-ether / dimethylformamide / 36 h / 40 °C
3: 5N NaOH / ethanol / 0.83 h / Heating
4: TFA / CH2Cl2 / 3 h / Ambient temperature
5: 98 percent / imidazole / dimethylformamide / 14 h / Ambient temperature
6: 97 percent / p-toluenesulfonyl chloride, pyridine / 24 h / Heating
7: 55 percent / isoamyl nitrite, CH2I2 / 0.33 h / 100 °C
8: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
9: NH3 / methanol
10: 70 percent / NH3 / methanol / 12 h / 120 °C
11: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: 97 percent / p-toluenesulfonyl chloride, pyridine / 24 h / Heating
2: 55 percent / isoamyl nitrite, CH2I2 / 0.33 h / 100 °C
3: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
4: NH3 / methanol
5: 70 percent / NH3 / methanol / 12 h / 120 °C
6: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: K2CO3, 18-crown-6-ether / dimethylformamide / 36 h / 40 °C
2: 5N NaOH / ethanol / 0.83 h / Heating
3: TFA / CH2Cl2 / 3 h / Ambient temperature
4: 98 percent / imidazole / dimethylformamide / 14 h / Ambient temperature
5: 97 percent / p-toluenesulfonyl chloride, pyridine / 24 h / Heating
6: 55 percent / isoamyl nitrite, CH2I2 / 0.33 h / 100 °C
7: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
8: NH3 / methanol
9: 70 percent / NH3 / methanol / 12 h / 120 °C
10: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: 70 percent / NH3 / methanol / 12 h / 120 °C
2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
2: NH3 / methanol
3: 70 percent / NH3 / methanol / 12 h / 120 °C
4: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: 55 percent / isoamyl nitrite, CH2I2 / 0.33 h / 100 °C
2: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
3: NH3 / methanol
4: 70 percent / NH3 / methanol / 12 h / 120 °C
5: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295
反应条件
1: 98 percent / imidazole / dimethylformamide / 14 h / Ambient temperature
2: 97 percent / p-toluenesulfonyl chloride, pyridine / 24 h / Heating
3: 55 percent / isoamyl nitrite, CH2I2 / 0.33 h / 100 °C
4: (PhCN)2PdCl2 / acetonitrile / 14 h / 100 °C
5: NH3 / methanol
6: 70 percent / NH3 / methanol / 12 h / 120 °C
7: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature
View Scheme
参考文献
Minakawa; Sasabuchi; Kiyosue; Kojima; Matsuda
Chemical and Pharmaceutical Bulletin, 1996 , vol. 44, # 2 p. 288 - 295