Novel 1,2,3-Triazole-Bisphenol-Based Macrocycle Synthesized Through Click Chemistry

被引:1
|
作者
Khan, Burhan [1 ]
Nadeem, Said [1 ,2 ]
Shah, Muhammad R. [1 ]
Yousuf, Sammer [1 ]
Hoda, Numan [2 ]
机构
[1] Univ Karachi, Int Ctr Chem & Biol Sci, HEJ Res Inst Chem, Karachi 75270, Pakistan
[2] Akdeniz Univ, Dept Chem, TR-07058 Antalya, Turkey
关键词
Bisphenol; click chemistry; 1,3-dipolar cycloadditions; macrocycles; 1,2,3-triazole; SHAPE-PERSISTENT MACROCYCLE; RECOGNITION; BINOL;
D O I
10.2174/15701786113109990040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A flexible macrocycle 7 based on 1,2,3-triazole and biphenol was synthesized through click chemistry and it contained propyl group. Click chemistry was used to get macrocycle 7 by reacting diazide 4 and diyne 6 in the presence of ascorbic acid. EI-MS of macrocycle 7 showed molecular ion peak at 614.3 while ESI-MS showed 615.25 [M+H](+). H-1 NMR of 7 showed the proton of propyl -CH2- at 2.26, 3.81 and 4.56 ppm while a singlet was observed at 5.26 ppm which belonged to methylene protons located between triazole ring and phenol. The aromatic proton at triazole ring was observed at 8.17 ppm while the protons of biphenyl were observed between 6.42 and 7.50 ppm. Crystallographic data of 3 were submitted to CCDC library (893412).
引用
收藏
页码:752 / 757
页数:6
相关论文
共 50 条
  • [41] A highly efficient and selective synthesis of 1,2,3-triazole linked saccharide nucleosides via "click chemistry"
    Ding, Haixin
    Yang, Ruchun
    Song, Yang
    Xiao, Qiang
    Wu, Jun
    [J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2008, 27 (04): : 368 - 375
  • [42] Exploiting the 1,2,3-Triazole Moiety to Generate Carbazole Molecular Architectures through Click Approach
    Ameen, Mohamed A.
    El-Shaieb, Kamal M.
    Mohamed, Asmaa H.
    Abdel-Latif, Fathy F.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (06) : 1718 - 1722
  • [43] 1,2,3-Triazolium-Based Poly(ionic liquid)s Obtained Through Click Chemistry Polyaddition
    Abdelhedi-Miladi, Imen
    Obadia, Mona M.
    Allaoua, Imene
    Serghei, Anatoli
    Ben Romdhane, Hatem
    Drockenmuller, Eric
    [J]. MACROMOLECULAR CHEMISTRY AND PHYSICS, 2014, 215 (22) : 2229 - 2236
  • [44] RAFT polymerization of bromotyramine-based 4-acryloyl-1,2,3-triazole: a functional monomer and polymer family through click chemistry
    Andjouh, Sofyane
    Bressy, Christine
    Blache, Yves
    [J]. RSC ADVANCES, 2016, 6 (18): : 14496 - 14504
  • [45] A Simple Efficient Click Synthesis of Novel Crown Ethers Containing 1,2,3-Triazole Moieties
    H. Elamari
    A. Ouerghui
    F. Ammari
    C. Girard
    [J]. Russian Journal of Organic Chemistry, 2019, 55 : 1785 - 1790
  • [46] Synthesis and Antibacterial Evaluation of 1,2,3-Triazole-based Quinazolines Using Click Chemistry in the Presence of Salophen Schiff Base Ligand
    Kazemi, Shaghayegh Sadat
    Keivanloo, Ali
    Nasr-Isfahani, Hossein
    Amin, Amir Hossein
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (07) : 1651 - 1657
  • [47] Poly(ethylene glycol)-Based Poly(ionic liquid) Block Copolymers through 1,2,3-Triazole Click Reactions
    Niskanen, Jukka
    Tousignant, Mathieu N.
    Peltekoff, Alexander J.
    Lessard, Benoit H.
    [J]. ACS APPLIED POLYMER MATERIALS, 2022, 4 (03) : 1559 - 1564
  • [48] A Simple Efficient Click Synthesis of Novel Crown Ethers Containing 1,2,3-Triazole Moieties
    Elamari, H.
    Ouerghui, A.
    Ammari, F.
    Girard, C.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (11) : 1785 - 1790
  • [49] Synthesis of novel heteroarenes based [1,2,3]-triazoles via click chemistry and their evaluation for antibacterial activity
    Prasad, Davinder
    Aggarwal, Nisha
    Kumar, Rajesh
    Nath, Mahendra
    [J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (05): : 731 - 738
  • [50] Click Chemistry Aided Synthesis of 1,4-Substituted 1,2,3-Triazole Based N-Fmoc Protected ε-Amino Acids: Isolation, Characterization and Synthesis of Novel Triazole Based Unnatural Amino Acids
    Sureshbabu, Vommina V.
    Narendra, N.
    Hemantha, H. P.
    Chennakrishnareddy, G.
    [J]. PROTEIN AND PEPTIDE LETTERS, 2010, 17 (04): : 499 - 506