以邻苯二胺及2,3-二氨基吡啶为原料,与羰基化合物反应制备苯并吡嗪、吡啶并吡嗪、苯并咪唑和吡啶并咪唑4种氮杂双环化合物,探讨了溶剂、温度、时间和pH值等实验条件对反应的影响.在合成吡啶并吡嗪时,采用正丙醇为溶剂,用甲醇钠调节pH =9,回流反应1h,将收率从35.7％提高至89.4％；在合成苯并吡嗪时,用水作溶剂,用亚硫酸钠调节pH =9,60℃反应40 min,产物纯化采用低温静置代替减压蒸馏,收率可提高至98.3％；尝试不同方法合成苯并咪唑和吡啶并咪唑,确定最优合成条件分别为:邻苯二胺在88％的甲酸溶液中回流2h,苯并咪唑收率为92％；2,3-二氨基吡啶在原甲酸三已酯中回流3h,加浓盐酸继续回流1h,吡啶并咪唑收率为84.2％.
参考文献
| [1] | LI Leping.Study on the Synthesis of Nitrogen Containing Heterocycles[D].Tianjin:Tianjin University,2004 (in Chinese).李乐平.含氮杂环化合物的合成研究[D].天津:天津大学,2004. |
| [2] | QIAN Qun.Synthesis,Characterization and Bioactivity of Heterocompounds Containing Pyridine Moieties[D].Shanghai:Shanghai University,2008 (in Chinese).钱群.含吡啶母环杂环化合物的合成、表征及生物活性研究[D].上海:上海大学,2008. |
| [3] | Nicolas Candelon,Svitlana Shinkaruk,Bernard Bennetau.New Approach to Asymmetrically Substituted Methoxypyrazines,Derivatives of Wine Flavors[J].Tetrahedron,2010,66:2463-2469. |
| [4] | Darren L N,Kay R B.Pressure Effects on the Thermal Decomposition of Nitramines,Nitrosamines and Nitrate Esters[J].J Org Chem,1992,57 (12):3303-3308. |
| [5] | Cavagnol J C,Wiselogle F Y.1-Alkyl-1,2,3,4-tetrahydroquinoxalines[J].J Am Chem Soc,1947,69:795-799. |
| [6] | ZHU Kangling,LI Meiqing,LI Guangxing.The Research on Selective Synthesis of Keto-isophorone[J].Chinese J Chem Reag,2004,26 (5):293-294 (in Chinese).朱康玲,李美清,李光兴.2,3-吡嗪二甲酸合成方法的改进[J].化学试剂,2004,26(5):293-294. |
| [7] | Petrow V,Sape J.Some 5-Azaquinoxalines and 4-Azabenziminazoles[J].J Chem Soc,1948,282:1389-1392. |
| [8] | Michael C V.2,3-Dihydroxy-Ⅰ,4-dioxane:A Stable Synthetic Equivalent of Anhydrous Glyoxal[J].Communications,1982:61-63. |
| [9] | Ansari K F.Synthesis,Physicochemical Properties and Antimicrobial Activityof Some New Benzimidazole Derivatives[J].Eur J Med Chem,2009,44:4028-4033. |
| [10] | Markus Clemenz,Bart Staels,Thomas Unger.Characterization of New PPAR? Agonists:Analysis of Telmisartan's Structural Components[J].Chem:Med Chem,2009,4:445-456. |
| [11] | Wanner M J,Rodenko B,Koch M,et al.New (1-Deaza) Purine Derivatives via Efficient C-2 Nitration of the (1-Deaza)Purine Ring[J].Nucleosides,2004,23:1313-1320. |
| [12] | David D Boehr,Adam R Farley,Frank J LaRonde.Establishing the Principles of Recognition in the Adenine-Binding Region of an Aminoglycoside Antibiotic Kinase[APH (3')-Ⅲ a][J].Biochemistry,2005,44:12445-12453. |
| [13] | Wael Zeinyeh,Julien Pilmé,Sylvie Radix.Regioselective N-Alkylation of Imidazo[4,5-b]pyridine-4-oxide Derivatives:An Experimental and DFT Study[J].Tetrahedron Lett,2009,50:1828-1833. |
| [14] | SUO Fuxi,HANG Yechao,XU Jianqiang,et al.Experimental Study on Identification of Aldehydes and Ketones with the Addition of Sodium Bisulfite[J].Chinese J Chem Educ,2008,5:68 (in Chinese).索福喜,杭烨超,徐建强,等.用亚硫酸氢钠加成法鉴别醛酮的实验研究[J].化学教育,2008,5:68. |
上一张
下一张
上一张
下一张
计量
- 下载量()
- 访问量()
文章评分
- 您的评分：
-
10%
-
20%
-
30%
-
40%
-
50%