한국응용과학기술학회지 (Journal of the Korean Applied Science and Technology)

  • 제25권3호
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  • Pages.291-298
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  • 2008
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  • 1225-9098(pISSN)
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  • 2288-1069(eISSN)
한국응용과학기술학회 (The Korean Society of Applied Science and Technology)
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Synthesis of N,N-Diaryl-(pyridin-3-yl)pyrimidin-2-amine Derivatives and Their Photochemical Properties

  • El-Deeb, Ibrahim Mustafa (Department of Biomolecular Science, University of Science and Technology) ;
  • Lee, So-Ha (Life Sciences Research Division, Korea Institute of Science and Technology)
  • 발행 : 2008.09.30
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초록

Although the pyrimidine derivatives were obtained in low yields ranging from 8% to 20%, we reported the successful preparation of N,N-diaryl-pyrimidin-2-amine derivatives starting from the corresponding 2-aminopyrimidines (1a-1c), by direct palladium-catalyzed arylation using different arylbromides. The reasons of low yields are thought to be the electronic and steric effects by the neighboring aromatic systems. The absorption spectra and photoluminescent spectra of compounds (3a 3g and 4a-4c) were measured using dichloromethane on the concentration of 25 mM by UV vis spectroscopy and luminescent spectroscopy. Pyrimidine derivatives 4a, 4b, and 4c showed moderate emission maxima at 474 nm, 481 nm, and 367 nm, respectively, while other compounds showed very weak photoluminescence or no photoluminescence at all.

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참고문헌

  1. Y. Fang, R. Karisch and M. Lautens, Efficient syntheses of KDR kinase inhibitors using a Pd-catalyzed tandem C-N/Suzuki coupling as the key step. J. Org. Chem., 72, 1341(2007) https://doi.org/10.1021/jo062228w
  2. Y. C. Ku, Y. S. Yen, T. H. Huang, C. H. Chen, J. T. Lin, and C. T. Tsai, Organic electroluminescent bis(diarylamino) dibenzofuran derivatives. J. Chinese Chem. Soc., 53, 1317 (2006) https://doi.org/10.1002/jccs.200600176
  3. H. B. Goodbrand and N. X. Hu, Ligand-accelerated catalysis of the Ullmann condensation: application to hole conducting triarylamines. J. Org. Chem., 64, 670 (1999) https://doi.org/10.1021/jo981804o
  4. J. P. Wolfe, S. Wagaw, and S. L. Buchwald, An improved catalyst system for aromatic carbon-nitrogen bond formation: The possible involvement of bis(phosphine)palladium complexes as key intermediates. J. Am. Chem. Soc., 118, 7215 (1996) https://doi.org/10.1021/ja9608306
  5. X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, and S. L. Buchwald, Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions. J. Am. Chem. Soc., 125, 6653 (2003) https://doi.org/10.1021/ja035483w
  6. M. D. Charles, P. Schultz, and S. L. Buchwald, Efficient Pd-catalyzed amination of heteroaryl halides. Org. Lett., 7, 3965 (2005) https://doi.org/10.1021/ol0514754
  7. K. W. Anderson, R. E. Tundel, T. Ikawa, R. A. Altman, and S. L. Buchwald, Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles. Angew. Chem. Int. Ed., 45, 6523 (2006) https://doi.org/10.1002/anie.200601612
  8. D. S. Surry and S. L. Buchwald, Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines. J. Am. Chem. Soc., 129, 10354 (2007) https://doi.org/10.1021/ja074681a
  9. R. A. ltman, B. P. Fors, and S. L. Buchwald, Pd-catalyzed amination reactions of aryl halides using bulky biarylmonophosphine ligands. Nat. Protoc., 2, 2881 (2007) https://doi.org/10.1038/nprot.2007.414
  10. Y. Harrak, M. Romero, P. Constans, and M. D. Pujol, Preparation of diarylamines and arylhydrazines using palladium catalysts. Lett. Org. Chem., 3, 29 (2006) https://doi.org/10.2174/157017806774964503
  11. X. Wang, D. V. Gribkov, and D. Sames, Phosphine-free palladium-catalyzed C-H Bond arylation of free (N-H)-indoles and pyrroles. J. Org. Chem., 72, 1476 (2007) https://doi.org/10.1021/jo061979v
  12. A. Salcedo, L. Neuville, C. Rondot, P. Retailleau, and J. Zhu, Palladium-catalyzed domino intramolecular N-arylation/intermolecular C-C bond formation for the synthesis of functionalized benzodiazepinediones. Org. Lett., 10, 857 (2008) https://doi.org/10.1021/ol7029799
  13. F. N. Ngassa, K. A. DeKorver, T. S. Melistas, E. A. Yeh, and M. K. Lakshman, Pd-Xantphos-catalyzed direct arylation of nucleosides. Org. Lett., 8, 4613 (2006) https://doi.org/10.1021/ol0619516
  14. I. M. El-Deeb, J. C. Ryu, and S. H. Lee, Synthesis of new N-arylpyrimidin-2-amine derivatives using a palladium catalyst. Molecules, 13, 818 (2008) https://doi.org/10.3390/molecules13040818
  15. A. H. Ismail, One pot synthesis of 1-(s-triazolo[4,3-c]pyrimidin-3-yl)substitut ed polyols. Synth. Commun., 32, 1791 (2002) https://doi.org/10.1081/SCC-120004057
  16. W. S. Hwang and W. C. Shakespeare, An efficient synthesis of nilotinib (AMN107). Synthesis, 14, 2121 (2007)