11-环丙基-5,11-二氢-4-(羟基甲基)-6H-二吡啶并[3,2-b:2',3'-e][1,4]二氮杂卓-6-酮合成路线 （共 12 条）
反应条件
1: 1.) SOCl2 / 1.) CH2Cl2, RT, 3.5 h, 2.) DMSO; a.) from 50 deg C to 60 deg C, 4 d, b.) RT, 18 d 2: 33 percent / 1.) KO-t-Bu, 2.) 30percent aq. oxalic acid / 1.) THF, DMSO, -10 deg C, 1 h, 2.) THF, reflux, 1 h View Scheme
参考文献
Klunder
Journal of Heterocyclic Chemistry, 1995 , vol. 32, # 6 p. 1687 - 1691
反应条件
1.1: 71 percent / N-chlorosuccinimide / CH2Cl2 / 1 h / 0 - 5 °C
2.1: 56 percent / 2-t-butyl-4-methylphenol / toluene / 2 h / 90 - 95 °C
3.1: 49 percent / sodium carbonate / toluene / 2 h / 90 - 100 °C
4.1: 83.6 percent / xylene / 72 h / 105 °C
5.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
6.1: trifluoroacetic acid / 168 h
7.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
7.2: tetrahydrofuran / 1 h / 20 °C
8.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
9.1: ozone / methanol / 0.17 h / -40 °C
9.2: methyl sulfide / methanol
9.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: 49 percent / sodium carbonate / toluene / 2 h / 90 - 100 °C
2.1: 83.6 percent / xylene / 72 h / 105 °C
3.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
4.1: trifluoroacetic acid / 168 h
5.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
5.2: tetrahydrofuran / 1 h / 20 °C
6.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
7.1: ozone / methanol / 0.17 h / -40 °C
7.2: methyl sulfide / methanol
7.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: thionyl chloride / 4 h / Heating
2.1: 49 percent / sodium carbonate / toluene / 2 h / 90 - 100 °C
3.1: 83.6 percent / xylene / 72 h / 105 °C
4.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
5.1: trifluoroacetic acid / 168 h
6.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
6.2: tetrahydrofuran / 1 h / 20 °C
7.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
8.1: ozone / methanol / 0.17 h / -40 °C
8.2: methyl sulfide / methanol
8.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: 56 percent / 2-t-butyl-4-methylphenol / toluene / 2 h / 90 - 95 °C
2.1: 49 percent / sodium carbonate / toluene / 2 h / 90 - 100 °C
3.1: 83.6 percent / xylene / 72 h / 105 °C
4.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
5.1: trifluoroacetic acid / 168 h
6.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
6.2: tetrahydrofuran / 1 h / 20 °C
7.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
8.1: ozone / methanol / 0.17 h / -40 °C
8.2: methyl sulfide / methanol
8.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: 49 percent / sodium carbonate / toluene / 2 h / 90 - 100 °C
2.1: 83.6 percent / xylene / 72 h / 105 °C
3.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
4.1: trifluoroacetic acid / 168 h
5.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
5.2: tetrahydrofuran / 1 h / 20 °C
6.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
7.1: ozone / methanol / 0.17 h / -40 °C
7.2: methyl sulfide / methanol
7.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: 83.6 percent / xylene / 72 h / 105 °C
2.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
3.1: trifluoroacetic acid / 168 h
4.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
4.2: tetrahydrofuran / 1 h / 20 °C
5.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
6.1: ozone / methanol / 0.17 h / -40 °C
6.2: methyl sulfide / methanol
6.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: trifluoroacetic acid / 168 h
2.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
2.2: tetrahydrofuran / 1 h / 20 °C
3.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
4.1: ozone / methanol / 0.17 h / -40 °C
4.2: methyl sulfide / methanol
4.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1.1: 54 percent / sodium hydride; pyridine / 1 h / 75 - 85 °C
2.1: trifluoroacetic acid / 168 h
3.1: sodium hydride / tetrahydrofuran / 0.25 h / -78 °C
3.2: tetrahydrofuran / 1 h / 20 °C
4.1: 28 percent / sodium iodide; trifluoroacetic acid / acetonitrile / 0 °C
5.1: ozone / methanol / 0.17 h / -40 °C
5.2: methyl sulfide / methanol
5.3: 45 percent / sodium borohydride / methanol / 2 h / 0 °C
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
反应条件
1: CH2Cl2 / 1 h / 20 °C
2: 20 percent / sodium borohydride; aq. sodium bicarbonate / CH2Cl2
View Scheme
参考文献
Grozinger, Karl G.; Byrne, Denis P.; Nummy, Laurence J.; Ridges, Michael D.; Salvagno, Annette
Journal of Heterocyclic Chemistry, 2000 , vol. 37, # 2 p. 229 - 239
