Bulletin of the Korean Chemical Society

  • 제32권2호
  • /
  • Pages.547-552
  • /
  • 2011
  • /
  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Polymers Including Both Triazole and Tetrazole by Click Reaction

  • 투고 : 2010.05.04
  • 심사 : 2010.12.06
  • 발행 : 2011.02.20
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Azido contained polymers were treated with various substituted N-propargyl tetrazoles in $CH_2Cl_2/H_2O$ at room temperature by Cu-catalyzed [2+3] cycloaddition to afford high yields of the corresponding polymers, possessing both triazole and tetrazole moiety.

키워드

참고문헌

  1. Fournier, D.; Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2007, 1369-1380.
  2. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262. https://doi.org/10.1039/b613014n
  3. Gil, M. V.; Arevalo, M. J.; Lopez, O. Synthesis 2007, 1589-1620.
  4. Lutz, J.-F. Angew. Chem. Int. Ed. 2007, 46, 1018-1025. https://doi.org/10.1002/anie.200604050
  5. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015. https://doi.org/10.1021/cr0783479
  6. Binder, W. H.; Sachsenhofer, R. Macromol. Rapid Commun. 2008, 29, 952-981. https://doi.org/10.1002/marc.200800089
  7. Jung, J.-H.; Lim, Y.-G.; Lee, K.-H.; Koo, B. T. Tetrahedron Lett. 2007, 48, 6442-6448. https://doi.org/10.1016/j.tetlet.2007.07.096
  8. Licht, H. H.; Ritter, H. J. Energ. Mater. 1994, 12, 223. https://doi.org/10.1080/07370659408018652
  9. Licht, H. H.; Ritter, H. Propell. Explos. Pyrotech. 1997, 22, 333. https://doi.org/10.1002/prep.19970220607
  10. Ostrovskii, V. A.; Pevzner, M. S.; Kofmna, T. P.; Shcherbinin, M. B.; Tselinskii, I. V. Targets Heterocycl. Syst. 1999, 3, 467.
  11. Hiskey, M.; Chavez, D. E.; Naud, D. L.; Son, S. F.; Berghout, H. L.; Bome, C. A. Proc. Int. Pyrotech. Semin. 2000, 27, 3.
  12. Kofman, T. P. Russ. J. Org. Chem. 2002, 38, 1231-1243.
  13. Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem. Int. Ed. 2006, 45, 3584-3601. https://doi.org/10.1002/anie.200504236
  14. Klapotke, T. M. Structure and Bonding : High Energy Density Compounds; Springer: Berlin/Heidelberg, 2007; Vol. 125.
  15. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Prog. Med. Chem. 1980, 17, 151. https://doi.org/10.1016/S0079-6468(08)70159-0
  16. Alvarez, R.; Velazquez, S.; San-Felix, A.; Aquaro, S.; DeClercq, E.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4194.
  17. Chem, X. M.; Li, Z. J.; Ren, Z. X.; Huang, Z. T. Carbohydr. Res. 1999, 315, 262. https://doi.org/10.1016/S0008-6215(99)00020-8
  18. Brockunier, L.; Parmee, E. R.; Ok, H. O.; Candelore, M. R.; Cascieri, M. A.; Colwell, L. F.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; MacIntyre, D. E.; Tota, L.; Wywratt, M. J.; Fisher, M. H.; Weber, A. E. Bioorg. Med. Chem. Lett. 2000, 10, 2111. https://doi.org/10.1016/S0960-894X(00)00203-1
  19. Ostrovskii, V. A.; Pevzner, M. S.; Kofman, T. P.; Tselinskii, I. V. Targets Heterocyclic syst. 1999, 3, 467.
  20. Drake, G.; Hawkins, T.; Brand, A.; Hall, L.; Mckay, M. Propell. Explos. Pyrotech. 2003, 28, 174. https://doi.org/10.1002/prep.200300002
  21. Tsarevsky, N. V.; Bernaerts, K. V.; Dufour, B.; Du Prez, F. E.; Matyjaszewski, K.; Macromolecules 2004, 37, 9308-9313. https://doi.org/10.1021/ma048207q
  22. Petrova, T. L.; Kizhnyaev, V. N.; Tsypina, N. A.; Vereshchagin, L. I.; Smirnov, A. I. Russian Pat. 2261873, 2005.
  23. Miller, C. G.; Williams, G. K. U. S. Pat. US 2007/0040167 A1, 2007.
  24. Kizhnyaev, V. N.; Pokatilov, F. A.; Vereshchagin, L. I. Polym. Sci. Ser. A 2007, 49, 28-34.
  25. Reddy, T. S.; Satpute, R. S.; Nair, J. K.; Gore, G. M.; Sikder, A. K. J. Polym. Mater. 2008, 25, 557-562.
  26. Tian, J.; Wan, L.; Huang, J.; Hu, Y.; Huang, F.; Du, L. Polym. Bull. 2008, 60, 457-465. https://doi.org/10.1007/s00289-007-0878-2
  27. Gromadzki, D.; Lokaj, J.; Cernoch, P.; Diat, O.; Nallet, F.; Štepánek, P. Eur. Polym. J. 2008, 44, 189-199. https://doi.org/10.1016/j.eurpolymj.2007.10.029
  28. Kizhnyaev, V. N.; Pokatilov, F. A.; Vereshchagin, L. I.; Verkhozina, O. N.; Petrova, T. L.; Prodaikov, A. G.; Ratovskii, G. V.; Tyukalova, O. V. Russ. J. Appl. Chem. 2009, 82, 1769-1775. https://doi.org/10.1134/S1070427209100048
  29. Klapotke, T. M.; Sproll, S. M. J. Polym. Sci.: Part A: Polym. Chem. 2010, 48, 122-127. https://doi.org/10.1002/pola.23767
  30. Klapotke, T. M.; Sproll, S. M. Eur. J. Org. Chem. 2010, 1169-1175.
  31. Govokov, A. T.; Fomina, M. P.; Bannova, E. A. High Energy Chem. 1990, 24, 439.
  32. Verkhozina, O. N.; Kizhnyaev, V. N.; Vereshchagin, L. I.; Rokhin, A. V.; Smirnov, A. I. Russ. J. Org. Chem. 2003, 39, 1792-1796. https://doi.org/10.1023/B:RUJO.0000019746.10504.f3
  33. Ye, C.; Gard, G. L.; Winter, R. W.; Syvret, R. G.; Twamley, B.; Shreeve, J. M. Org. Lett. 2007, 9, 3841-3844. https://doi.org/10.1021/ol701602a
  34. Helms, B.; Mynar, J. L.; Hawker, C. J.; Fréchet, J. M. J. J. Am. Chem. Soc. 2004, 126, 15020-15021. https://doi.org/10.1021/ja044744e
  35. Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M. J.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928-3932. https://doi.org/10.1002/anie.200454078
  36. Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem. Int. Ed. 2005, 44, 2210-2215. https://doi.org/10.1002/anie.200461496
  37. Lee, B. Y.; Park, S. R.; Jeon, H. B.; Kim, K. S. Tetrahedron Lett. 2006, 47, 5105-5109.
  38. Verkhozina, O. N.; Kizhnyaev, V. N.; Vereshchagin, L. I.; Rokhin, A. V.; Smirnov, A. I. Russ. J. Org. Chem. 2003, 39, 1792-1796. https://doi.org/10.1023/B:RUJO.0000019746.10504.f3
  39. Koyama, M.; Ohtani, N.; Kai, F.; Moriguchi, I.; Inouye, S. J. Med. Chem. 1987, 30, 552-562. https://doi.org/10.1021/jm00386a019

피인용 문헌

  1. Synthesis and proton conductivity studies of methacrylate/methacrylamide-based azole functional novel polymer electrolytes vol.131, pp.4, 2013, https://doi.org/10.1002/app.39915
  2. 5-(methacrylamido)tetrazole and vinyl triazole based copolymers as novel anhydrous proton conducting membranes vol.20, pp.9, 2013, https://doi.org/10.1007/s10965-013-0242-1
  3. Synthesis and characterization of new nitrogen-rich polymers as candidates for energetic applications vol.17, pp.5, 2014, https://doi.org/10.1080/15685551.2013.867569
  4. Novel composite polymer electrolyte membranes based on poly(vinyl phosphonic acid) and poly (5-(methacrylamido)tetrazole) vol.55, pp.2, 2014, https://doi.org/10.1002/pen.23890
  5. Preparation of Azidated Polybutadiene(Az-PBD)/Ethylene-Vinyl Acetate Copolymer(EVA) Blends for the Application of Energetic Thermoplastic Elastomer vol.53, pp.3, 2015, https://doi.org/10.9713/kcer.2015.53.3.282
  6. Terminal bis-acetylenes derived from 1,2-bis(1H-tetrazol-5-yl)ethane vol.65, pp.5, 2016, https://doi.org/10.1007/s11172-016-1446-4
  7. Tailoring of energetic groups in acroyloyl polymers vol.20, pp.1, 2017, https://doi.org/10.1080/15685551.2016.1258977
  8. “High-Throughput” Evaluation of Polymer-Supported Triazolic Appendages for Metallic Cations Extraction vol.5, pp.1, 2015, https://doi.org/10.3390/met5010418
  9. Synthesis and Characterization of Polystyrene-Supported Piperazine-Substituted Triazoles by CuAAC and First Evaluation for Metal Ion Extraction vol.8, pp.5, 2016, https://doi.org/10.3390/polym8050187
  10. Nitramine-Group-Containing Energetic Prepolymer: Synthesis, and Its Properties as a Binder for Propellant vol.11, pp.12, 2011, https://doi.org/10.3390/polym11121966