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水溶剂中β-环糊精促进炔丙苷、溴代烷烃和叠氮化钠缩合生成1,2,3-三氮唑衍生物 被引量：1

β-Cyclodextrin-promoted condensation of propargyl glycosides,alkanyl bromides,and sodium azide to prepare 1,2,3-triazole derivatives in water
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摘要 本文报到了一种以β-D-炔丙苷、溴代烷烃、叠氮化钠为原料,仅以水为溶剂、Cu(I)催化、β-环糊精为相转移催化剂,室温下采用"一锅煮"法,高效、绿色、高区域选择性的合成了系列1,2,3-三氮唑缀合的糖苷衍生物(产率72-88%)。 An efficient and environment-friendly synthesis of 1,2,3-triazolyl glycoside derivatives was successfully established viathe condensation of propargyl β-D-glycosides,alkanyl bromides,and sodium azide（yield 72-88%）. This one-pot,Cu（I）-catalyzed,cyclodextrin-promoted process was carried out in only water at room temperature with high regioselectivity.
作者 刘燕 顾振龙 何彩玉 柏俊 程杰
机构地区 安徽省食品药品信息与举报中心 安徽食品药品检验研究院科研办公室(原安徽省药物研究所) 安徽中医药大学药学院
出处 《化学研究与应用》 CAS CSCD 北大核心 2014年第11期1793-1797,共5页 Chemical Research and Application
基金 安徽省自然科学基金项目(1208085QB23)资助
关键词 1 2 3-三氮唑 糖苷 环糊精 1 3-偶极环加成 绿色化学 1,2,3-triazole glycoside cyclodextrin 1,3-dipolar cycloaddition green chemistry
分类号 O621.3 [理学—有机化学]
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参考文献12

  • 1胡晓燕,孙翠兰,冷传新,朱屹东,初乐玲,王晶翼.三氮唑类化合物的合成及抗真菌活性研究[J].化学研究与应用,2010,22(12):1573-1577. 被引量：3
  • 2Kolb H C,Sharpless K B. The growing impact of clickchemistry on drug discovery [J]. Drug Discov Today,2003,8:1 128-1 137.
  • 3Silva F C,Souza M C,Frugulhetti I I,et al. Synthesis HIVRTinhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazolederivatives of carbohydrates[J]. Eur J Med Chem,2009,44:373-383.
  • 4Rostovtsev V V,Green L G,Fokin V V,et al. First Cu Icatalyzed“ click” reactions between alkynes and azides[J]. Angew Chem Int Ed,2002,42:2 596-2 599.
  • 5Rad M N,Behrouz S,Doroodmand M M. Copper-doped silicacuprous sulfate(CDSCS)as a highly efficient and newheterogeneous nano catalyst for[3+2]Huisgen cycloaddition[J]. Tetrahedron,2012,68:7 812-7 821.
  • 6Locos O B,Heindl C C,Corral A,et al. Efficient synthesisof glycoporphyrins by microwave-mediated“click”reactions[J]. Eur J Org Chem,2010,(6):1 026-1 028.
  • 7Vecchi A,Chambery A,Chiappe C,et al. Copper(I)-catalyzedazide-alkyne cycloadditions in ionic liquids under amine-free conditions [J]. Synthesis, 2010, 12: 2 043-2048.
  • 8Jung-Ah S,Yeong-Gweon L,Kyung-Hee L. Copper-catalyzedazide-alkyne cycloaddition reaction in water usingcyclodextrin as a phase transfer catalyst[J]. J Org Chem,2012,77:4 117-4 122.
  • 9Liu Q,Ji Y. Cu2 O acting as a robust catalyst in CuAAC reactions:water is the required medium[J]. Green Chem.2011,13:562-565.
  • 10夏娟,宋乐新,邵志成,陈杰.环糊精超分子包络物的相变行为及其热分析研究进展[J].化学研究与应用,2012,24(5):657-665. 被引量：2

二级参考文献16

  • 1Ostrosky-Zeichner L,Casadevall A,Galgiani J N,et al.An insight into the antifungal pipeline:selected new molecules and beyond[J].Nat.Rev.Drug Discov.,2010,9(9):719-727.
  • 2Rezaeia Z,Khabnadideha S,Pakshirb K,et al.Design,synthesis,and antifungal activity of triazole and benzotriazole derivatives[J].Eur.J.Med.Chem.,2009,44(7):3064-3067.
  • 3Freifeld A,Proia L,Andes D,et al.Voriconazole use for endemic ffungal infections[J].Antimicrob.Agents Chemother.,2009,53(4):1648-1651.
  • 4Salama S M,Atwal H,Gandhi A,et al.In vitro and in vivo activities of Syn2836,Syn2869,Syn2903,and Syn2921:new series of triazole antifungal aqgents[J].Antimicrob.Agents Chemother.,2001,45:2420-2426.
  • 5Luo Y,Lu Y H,Gan L L,et al.Synthesis,antibacterial and antifungal activities of novel 1,2,4-triazolium derivatives[J].Archiv.der.Pharmazie,2009,342(7):386-393.
  • 6Chai X,Zhang J,Yu S,et al.Design,synthesis,and biological evaluation of novel 1-(1H-1,2,4-triazole-1-yl)-2-(2,4-difluorophenyl)-3-substituted benzylamino-2-propanols[J].Bioorg.Med.Chem.Lett.,2009,19(6):1811-1814.
  • 7Bay H A,Quaddouri B,Guaadaoui A,et al.Synthesis and biological activity of new triazole compounds[J].Letters in Drug Design & Discovery,2010,7(1):41-45(5).
  • 8Mike Butters,Julie Ebbs,Stuart P.Green,et al.Process development of voriconazole:a novel broad-spectrum triazole antifungal agent[J].Organic Process Research & Development,2001,5:28-36.
  • 9Ostrosky-Zeichner L.,Rex J H,Pappas P G,et al.Antifungal susceptibility survey of 2,000 bloodstream candida isolates in the United States[J].Antimicrobial Agents and Chemotherapy,2003,47(10):3149-3154.
  • 10朱浩翔,张永信,章强强,龙丰.Neo-Sensitab纸片扩散法与NCCL SM27-A微量稀释法测定97株酵母对抗真菌药物敏感性的比较[J].中国抗生素杂志,2007,32(8):506-510. 被引量：5

共引文献3

同被引文献15

  • 1尚尔才,刘长令,杜英娟.吡啶类农药的研究进展(上)[J].化工进展,1996,15(5):11-14. 被引量：40
  • 2张濛,王歆宇,王万海,马新爱.两种方法检测抗菌剂抑菌效果的比较[J].中国消毒学杂志,2006,23(5):436-438. 被引量：11
  • 3Agalave S G, Maujan S R, Pore V S. Click chemistry: 1 ,2, 3-triazoles as pharmacophores[J]. Chern AsianJ,2011,6 (10) :2 696-2 718.
  • 4Kallander L S, Lu Q, Chen W F, et al. 4-Aryl-1 ,2, 3-triazole , a novel template for a reversible methionine aminopeptidase 2 inhibitor, optimized to inhibit angiogenesis in vivo[J].J Med (ifLem,2005,48(l8):5 644-5 647.
  • 5Rostovtsev V V, Green L G, Sharpless K B, et al. A stepwise Huisgen cycloaddition process: copper ( I) -catalyzed regioselective " ligation" of azides and terminal alkynes[J].Angew. Chem lnt Ed,2002,114(14):2 708-2 711.
  • 6Jiang Y Q, Mao L F, Zhu L, et al. Synthesis, characterization and antifungal evaluation of novel 2H-l ,4-benzoxazin- 3 (4H) -one derivatives linked with a 1 ,2 ,3-triazole moiety[J]. Z Naturforsch B ,2014 ,69b: 103-108.
  • 7Zhang L, Chen X G, Xue P , et al. Ruthenium-catalyzed cycloaddition of alkynes and organic azides[J] .] Am Chem Soc ,2005,127 (46) : 15 998-15 999.
  • 8Li WJ, Du Z Y, HuangJ Y, et al. Direct access to 1 ,2 , 3-triazoles through organocatalytic 1 ,3-dipolar cycloaddition reaction of allyl ketones with azides[J]. Green Chem,2014,16(6):3 003-3 006.
  • 9Ramachary DB, Shashank A B, Karthik S. An organocatalytic azide-aldehyde[3 + 2J cycloaddition , high Yielding regioselective synthesis of 1 ,4-disubstituted 1,2,3 -triazoles] J J. Angew Chem. Tnt Ed ,2014,53 (39) : 10 420-10 424.
  • 10Belkheira M, EI Abed D, PonsJ M, et al. Organocatalytic synthesis of 1 ,2 ,3-triazoles from unactivated ketones and arylazides] J J. Chem Eur],2011,17 (46): 12 917-12 921.

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化学研究与应用
2014年 第11期

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