Study of plant coumarins. 12*. Synthesis of 2-(1,2,3-triazolyl)-modified furocoumarins

被引:11
作者
Lipeeva, A. V. [1 ]
Shults, E. E. [1 ]
Makhneva, E. A. [1 ]
Shakirov, M. M. [1 ]
Tolstikov, G. A. [1 ]
机构
[1] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
基金
俄罗斯基础研究基金会;
关键词
alkynes; 2-bromooreoselone; dicoumarins; triazolylfurocoumarins; CLICK; 1,2,3-TRIAZOLES; INHIBITORS; CHEMISTRY; ANALOGS;
D O I
10.1007/s10593-013-1281-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bromooreoselone reacted with sodium azide to give 2-azidooreoselone, which was highly reactive in a catalytic Huisgen reaction with various terminal alkynes. These reactions yielded 4-substituted 2-(triazol-1-yl)furocoumarins. The reaction of oreoselone azide with dimethyl acetylene-1,2-di-carboxylate gave 2-[(4,5-dimethoxycarbonyl)triazolyl]oreoselone and reaction with 7-ethynyl-6-methoxycarbonylcoumarin gave 1,4-dicoumarin-substituted 1,2,3-triazole.
引用
收藏
页码:551 / 560
页数:10
相关论文
共 25 条
  • [1] N- and C-acyclic thionuleoside analogues of 1,2,3-triazole
    Al-Masoudi, NA
    Al-Soud, YA
    Abdul-Zahra, A
    [J]. HETEROATOM CHEMISTRY, 2004, 15 (05) : 380 - 387
  • [2] One-pot synthesis of triazole-linked glycoconjugates
    Chittaboina, S
    Xie, F
    Wang, Q
    [J]. TETRAHEDRON LETTERS, 2005, 46 (13) : 2331 - 2336
  • [3] Claramunt RM, 1997, MAGN RESON CHEM, V35, P35, DOI 10.1002/(SICI)1097-458X(199701)35:1<35::AID-OMR25>3.0.CO
  • [4] 2-K
  • [5] Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis
    Genin, MJ
    Allwine, DA
    Anderson, DJ
    Barbachyn, MR
    Emmert, DE
    Garmon, SA
    Graber, DR
    Grega, KC
    Hester, JB
    Hutchinson, DK
    Morris, J
    Reischer, RJ
    Ford, CW
    Zurenko, GE
    Hamel, JC
    Schaadt, RD
    Stapert, D
    Yagi, BH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (05) : 953 - 970
  • [6] Creation of 3,4-bis-triazolocoumarin-sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media
    He, Xiao-Peng
    Song, Zhuo
    Wang, Zhi-Zhou
    Shi, Xiao-Xin
    Chen, Kaixian
    Chen, Guo-Rong
    [J]. TETRAHEDRON, 2011, 67 (19) : 3343 - 3347
  • [7] The chemistry and biology of bicoumarins
    Hussain, Hidayat
    Hussain, Javid
    Al-Harrasi, Ahmed
    Krohn, Karsten
    [J]. TETRAHEDRON, 2012, 68 (12) : 2553 - 2578
  • [8] 7-Triazolylcoumarin-based fluorescent tag system for stepwise, comparative assessment of small molecule microarrays
    Jeon, Moon-Kook
    Kang, Myoung-Ku
    Park, Koon Ha
    [J]. TETRAHEDRON, 2012, 68 (30) : 6038 - 6053
  • [9] Expedient synthesis of triazole-linked glycosyl amino acids and peptides
    Kuijpers, BHM
    Groothuys, S
    Keereweer, AR
    Quaedflieg, PJLM
    Blaauw, RH
    van Delft, FL
    Rutjes, FPJT
    [J]. ORGANIC LETTERS, 2004, 6 (18) : 3123 - 3126
  • [10] A Click Fluorophore Sensor that Can Distinguish CuII and HgII via Selective Anion-Induced Demetallation
    Lau, Yu Heng
    Price, Jason R.
    Todd, Matthew H.
    Rutledge, Peter J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (10) : 2850 - 2858