在三甲基氯硅烷(TMSCl)的催化作用下,取代苯甲醛与邻(芳胺甲基)苯酚经N杂缩醛化反应生成了一系列2,3-二芳基-1,3-苯并噁嗪类化合物.目标化合物的结构用IR、1H NMR、”C NMR和元素分析等技术手段进行了表征.对所合成的化合物进行了初步杀菌活性测试,部分表现出良好的杀菌活性,化合物6e对菌核病菌的抑制活性为79.0％,化合物6a和6d均为74.8％,化合物6e对灰霉病菌的抑制活性为77.9％.
参考文献
| [1] | Leila Benameur;Zouhair Bouaziz;Pascal Nebois;Marie-Helene Bartoli;Michele Boitard;Houda Fillion.Synthesis of Furonaphth[l,3]oxazine and Furo[l,3]oxazinoquinoline Derivatives as Precursors for an 0-Quinomemethide Structure and Potential Antitumor Agents[J].Chemical and Pharmaceutical Bulletin,19963(3):605-608. |
| [2] | Wang S;Li Y;Liu Y;Lu A;You Q.Novel hexacyclic camptothecin derivatives. Part 1: synthesis and cytotoxicity of camptothecins with an A-ring fused 1,3-oxazine ring.[J].Bioorganic and Medicinal Chemistry Letters,200814(14):4095-4097. |
| [3] | Chen, S.;Li, X.;Wan, S.;Jiang, T..Synthesis of novel benzoxazinone compounds as epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors[J].Synthetic Communications,201219/21(19/21):2937-2946. |
| [4] | Urbanski T;Radzikowski C Z;Ledochowski Z.Biological Activity of Benzoxazine-1,3 Derivatives,Particularly Against Experimental Sarcoma[J].NATURE,1956178:1351-1352. |
| [5] | Ihmaid,S.K.;Al-Rawi,J.M.A.;Bradley,C.J.;Angove,M.J.;Robertson,M.N..Synthesis, DNA-PK inhibition, anti-platelet activity studies of 2-(N-substituted-3-aminopyridine)-substituted-1,3-benzoxazines and DNA-PK and PI3K inhibition, homology modelling studies of 2-morpholino-(7,8-di and 8-substituted)-1,3-benzoxazines[J].European Journal of Medicinal Chemistry: Chimie Therapeutique,2012:85-101. |
| [6] | Ujjinamatada, RK;Appala, RS;Agasimundin, YS.Synthesis and antimicrobial activity of new benzofuranyl-1,3-benzoxazines and 1,3-benzoxazin-2-ones[J].Journal of Heterocyclic Chemistry,20062(2):437-441. |
| [7] | Tang, Z.;Chen, W.;Zhu, Z.;Liu, H..Synthesis of 2,3-diaryl-3,4-dihydro-2H-1,3-benzoxazines and their fungicidal activities[J].Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry,20112(2):255-260. |
| [8] | Neme?ek, P.;Mocák, J.;Lehotay, J.;Waisser, K..Prediction of anti-tuberculosis activity of 3-phenyl-2H-1,3-benzoxazine-2, 4(3H)-dione derivatives(Conference Paper)[J].Chemicke Zvesti,20133(3):305-312. |
| [9] | Waisser K;Petrlikova E;Perina M.A Note to the Biological Activity of Benzoxazin Derivatives Containing the Thioxo Group[J].EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,201045:2715-2719. |
| [10] | Pastemak A;Goble S D;Struthers M.Discovery of a Potent and Orally Bioavailable CCR2 and CCR5 Dual Antagonist[J].ACS Med Chem Lett,20101:14-18. |
| [11] | Vikas Garg;Ankit Kumar;Anurag Chaudhary.Synthesis, biological evaluation and molecular docking studies of 1,3-benzoxazine derivatives as potential anticancer agents[J].Medicinal chemistry research: an international journal for rapid communications on design and mechanisms of action of biologically active agents,201311(11):5256-5266. |
| [12] | Craig A. Coburn;Peter T. Meinke;Wei Chang.Discovery of MK-8742: An HCV NS5A Inhibitor with Broad Genotype Activity[J].ChemMedChem,201312(12):1930-1940. |
| [13] | Baqar, M.;Agag, T.;Huang, R.;Maia, J.;Qutubuddin, S.;Ishida, H..Mechanistic pathways for the polymerization of methylol-functional benzoxazine monomers[J].Macromolecules,201220(20):8119-8125. |
| [14] | Kawaguchi A W;Sudo A;Endo T.Polymerization-Depolymerization System Based on Reversible Addition-Dissociation Reaction of 1,3-Benzoxazine with Thiol[J].ACS Macro Lett,20132:1-4. |
| [15] | Li, W.;Wei, T.;Gao, Y.;Xi, K.;Jia, X..Preparation of novel benzoxazine monomers containing ferrocene moiety and properties of polybenzoxazines[J].Polymer: The International Journal for the Science and Technology of Polymers,20126(6):1236-1244. |
| [16] | Tomasulo, M;Sortino, S;White, AJP;Raymo, FM.Fast and stable photochromic oxazines[J].The Journal of Organic Chemistry,200520(20):8180-8189. |
| [17] | Erhan Deniz;Massimiliano Tomasulo;Salvatore Sortino.Substituent Effects on the Photochromism of Bichromophoric Oxazines[J].The journal of physical chemistry, C. Nanomaterials and interfaces,200919(19):8491-8497. |
| [18] | Vladislava Voiciuk;Kipras Redeckas;Vytas Martynaitis.Improving the photochromic properties of indolo[2,1-b][1,3]benzoxazines with phenylic substituents[J].Journal of Photochemistry and Photobiology, A. Chemistry,2014:60-68. |
| [19] | Burke W J.3,4-Dihydro-1,3,2H-benzoxazines.Reacting of p-Substituted Phenols with N,N-Dimethylolamines[J].Journal of the American Chemical Society,194971:609-612. |
| [20] | Burke W J;Murdock K C;Grace E.Condensation of Hydroxyaromatic Compounds with Formaldehyde and Primary Aromatic Amines[J].Journal of the American Chemical Society,195476:1677-1679. |
| [21] | Mathew, BP;Nath, M.One-Pot Three-Component Synthesis of Dihydrobenzo- and Naphtho[e]-1,3-oxazines in Water[J].Journal of Heterocyclic Chemistry,20095(5):1003-1006. |
| [22] | 唐子龙;夏赞稳;马红伟;刘汉文;欧晓明.Mannich反应合成3,6（8）-二取代-2,4-二氢-1,3-苯并（口恶）嗪及其杀菌活性[J].应用化学,2013(9):993-998. |
| [23] | Colin J L;Loubinoux B.A New Route to 3,4-Dihydro-2H-1,3-benzoxazines[J].Tetrahedron Letters,198223:4245-4246. |
| [24] | McDonagh A F;Smith H E.Ring-chain Tautomerism of Derivatives of o-Hydroxybenzylamine with Aldehydes and Ketones[J].Journal of Organic Chemistry,196833:1-8. |
| [25] | Neuvonen K;Pihlaja K.Studies on the Benzoxazine Series.Part 1.Preparation and 1H and 13C Nuclear Magnetic Resonance Structural Study of Some Substituted 3,4-Dihydro-2H-1,3-benzoxazines[J].Journal of the Chemical Society,Perkin Transactions Ⅱ,1988:461467. |
| [26] | Istvan Szatmari;Tamas A.Martinek;Laszlo Lazar;Ferenc Fulop.Synthesis of 2,4-Diaryl-3,4-dihydro-2H-naphth[2,l-e][l,3]oxazines and Study of the Effects of the Substituents on Their Ring-Chain Tautomerism[J].European journal of organic chemistry,200410(10):2231-2238. |
| [27] | Ian K. Mangion;Cheng-yi Chen;Hongmei Li;Peter Maligres;Yonggang Chen;Melodie Christensen;Ryan Cohen;Ingyu Jeon;Artis Klapars;Shane Krska;Hoa Nguyen;Robert A. Reamer;Benjamin D. Sherry;Ilia Zavialov.Enantioselective Synthesis of an HCV NS5a Antagonist[J].Organic letters,20149(9):2310-2313. |
| [28] | Matthew T. Richers;Martin Breugst;Alena Yu. Platonova;Anja Ullrich;Arne Dieckmann;K. N. Houk;Daniel Seidel.Redox-Neutral α?Oxygenation of Amines: Reaction Development and Elucidation of the Mechanism[J].Journal of the American Chemical Society,201416(16):6123-6135. |
| [29] | Tang, Z.;Chen, W.;Zhu, Z.;Liu, H..SnCl _4-catalyzed aza-acetalization of aromatic aldehydes: Synthesis of aryl substituted 3,4-dihydro-2H-1,3-benzoxazines[J].Synthetic Communications,20127/9(7/9):1372-1383. |
| [30] | Tang Z;Zhu Z;Xia Z.Synthesis and Fungicidal Activity of Novel 2,3-Disubstituted-1,3-benzoxazines[J].MOLECULES,201217:8174-8185. |
| [31] | Tang, Z.;Zhu, Z.;Yan, L.;Chang, S.;Liu, H..Efficient synthesis of 2,3-disubstituted-1,3-benzoxazines by chlorotrimethylsilane-mediated aza-acetalizations of aromatic aldehydes[J].Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry,20135(5):1116-1120. |
| [32] | 唐子龙;常书红;颜林;崔美艳;刘汉文.新型3-（1,3,4-噻二唑基）-1,3-苯并噁嗪类化合物的合成和杀菌活性[J].有机化学,2012(7):1241-1246. |
| [33] | 唐子龙;夏赞稳;陆良秋.FeCl3·6H2O催化合成2,3-二取代-1,3-苯并噁嗪及其杀菌活性[J].华中师范大学学报（自然科学版）,2014(3):360-365,369. |
| [34] | 陈杰山.亲氧元素及元素的亲氧性[J].化学教育,2000(05):40. |
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%