以2-氨基-5-烃基-1,3,4-噻二唑和水杨醛为原料,分别用“分步法”和“一锅法”经还原中间产物Schiff碱的C=N双键合成了一系列2-((1,3,4-噻二唑基)胺甲基)苯酚类新化合物,“一锅法”的产率较高,为56％～80％.产物的结构用IR、1H NMR、13C NMR和MS进行了表征.初步测试了目标化合物的杀菌活性,证明化合物对赤星病菌具有较好的抑菌活性,当浓度为25 mg/L时,化合物3i的抑制率为76％,化合物3f、3h、3k和3l的为70％.
参考文献
| [1] | Stokker G E,Deana A A,deSolms D S,et al.2-(Aminomethyl) phenols,a New Class of Saluretic Agents.1.Effects of Nuclear Substitution[J].J Med Chem,1980,23:1414-1427. |
| [2] | Kragler A,Hofner G,Wanner K T.Synthesis and Biological Evaluation of Aminomethylphenol Derivatives as Inhibitors of the Murine GABA Transporters mGAT1emGAT4[J].Eur J Med Chem,2008,43:2404-2411. |
| [3] | Lee C H,Jin G F,Joung J G,et al.New Types of Potential BNCT Agents,o-Carboranyl Aminoalcohols[J].Tetrahedron Lett,2009,50:2960-2963. |
| [4] | Lawrence R M,Dennis K C,O'Neill P M,et al.Development of a Scalable Synthetic Route to GSK369796(N-tert-Butyl Isoquine),a Novel 4-Aminoquinoline Antimalarial Drug[J].Org Process Res Dev,2008,12:294-297. |
| [5] | Greatti A,Scarpellini M,Peralta R A,et al.Synthesis,Structure,and Physicochemical Properties of Dinuclear NiⅡ Complexes as Highly Efficient Functional Models of Phosphohydrolases[J].Inorg.Chem,2008,47:1107-1119. |
| [6] | Cimarelli C,Palmieri G.Alkylation of Dianions Derived from 2-(1-Iminoalkyl) Phenols:Synthesis of Functionalized 2-Acyl Phenols[J].Tetrahedron,1998,54:15711-15720. |
| [7] | Waisser K,Gregor K,Kubicova L,et al.New Groups of Antimycobacterial Agents:6-Chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 6-Chloro-3-phenyl-4-2H-1,3-benzoxazine-2,4(3H)-dithiones[J].Eur J Med Chem,2000,35:733-741. |
| [8] | Waisser K,Gregor K,Dostal H,et al.Influence of the Replacement of the Oxo Function with the Thioxo Group on the Antimycobacterial Activity of 3-Aryl-6,8-dichloro-2H-1,3-benzoxazine-2,4 (3H)-diones and 3-Arylquinazoline-2,4 (1H,3H)-diones[J].Il Farmaco,2001,56:803-807. |
| [9] | Pasternak A,Goble S D,Struthers M,et al.Discovery of a Potent and Orally Bioavailable CCR2 and CCR5 Dual Antagonist[J].ACS Med Chem Lett,2010,(1):14-18. |
| [10] | Tang Z,Chen W,Zhu H,et al.Synthesis of 2,3-Diaryl-3,4-dihydro-2H-1,3-benzoxazines and Their Fungicidal Activities[J].J Heterocycl Chem,2011,48:255-260. |
| [11] | Cimarelli C,Palmieri G,Volpini E.Ready N-alkylation of Enantiopure Aminophenols:Synthesis of Tertiary Aminophenols[J].Tetrahedron,2001,57:6089-6096. |
| [12] | Palmieri G.Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols:Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes[J].Eur J Org Chem,1999:805-811. |
| [13] | Palmieri G A.Practical o-Hydroxybenzylamines Promoted Enantioselective Addition of Dialkylzincs to Aldehydes with Asymmetric Amplification[J].Tetrahedron:Asymmetry,2000,11:3361-3373. |
| [14] | Huang W,Zhao P L,Liu C L,et al.Design,Synthesis,and Fungicidal Activities of New Strobilurin Derivatives[J].J Agric Food Chem,2007,55:3004-3010. |
| [15] | Cao S,Wei N,Zhao C,et al.Syntheses,Antifeodant Activity,and QSAR Analysis of New Oxa(thia) diazolyl 3(2H)-Pyridazinones[J].J Agric Food Chem,2005,53:3120-3125. |
| [16] | Tyman J H P,Patel M.Phenolic Structure and Colour in Mannich Reaction Products[J].J Chem Research,2007:34-37. |
| [17] | Shafiee A,Foroumadi A.Synthesis of Arylsulfonyl-1,3,4-thiadiazoles[J].Heterocycl Chem,1996,33:1611-1614. |
| [18] | TANG Zilong,ZHANG Chaoyi,LIU Hanwen,et al.Synthesis and Charaterization 1,3,4-Thiadiazole Substituted Schiff Bases[J].Fine Chem Intermed,2010,40(4):19-23 (in Chinese).唐子龙,张超逸,刘汉文,等.N-1,3,4-噻二唑基取代水杨醛Schiff碱的合成与表征[J].精细化工中间体,2010,40(4):19-23. |
| [19] | Liu A P,Ou X M,Huang M Z.Synthesis and Insecticidal Activity of Novel Oxime Ether Pyrethroids[J].Pest Manage Sci,2005,61:166-170. |
| [20] | Karakas A,Elmali A,(U)nver H,et al.Nonlinear Optical Properties of Some Derivatives of Salicylaldimine-based Ligands[J].J Mol Struct,2004,702:103-110. |
| [21] | Arod F,Gardon.M,Pattison P,etal.The α2-Polymorph of Salicylidene-aniline[J].Acta Cryst Sect C,2005,C61:0317-0320. |
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%