Issue

Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022

Copyright (c) 2022 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Influence of Solvent and Oxidant in Copper-Catalyzed Synthesis of Xanthine Skeletons

https://doi.org/10.14233/ajchem.2022.23741
Habibur Rahaman
Department of Chemistry, Ranaghat College, Nadia-741201, India

Corresponding Author(s) : Habibur Rahaman

hr1977@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 5 (2022): Vol 34 Issue 5, 2022

Abstract

An interesting approach for the synthesis of xanthine skeletons by a copper-catalyzed reaction between N,N′-dialkylated 5-bromouracil derivatives and amidines are being reported. The coupling reaction was promoted by catalytic amount of Cu(OAc)2 in the presence of molecular O2. The 1,4-dioxane was found to be a better solvent for the reaction and the reaction was believed to go through a N-arylation and subsequent C-H activation/C-N bond formation process.

Keywords

Copper Coupling reaction Xanthine C-H activation Molecular oxygen C-N Bond formation
Rahaman, H. (2022). Influence of Solvent and Oxidant in Copper-Catalyzed Synthesis of Xanthine Skeletons. Asian Journal of Chemistry, 34(5), 1310–1312. https://doi.org/10.14233/ajchem.2022.23741
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. I.P. Beletskaya and A.V. Cheprakov, Organometallics, 31, 7753 (2012); https://doi.org/10.1021/om300683c
  2. X. Chen, X.-S. Hao, C.E. Goodhue and J.-Q. Yu, J. Am. Chem. Soc., 128, 6790 (2006); https://doi.org/10.1021/ja061715q
  3. E.J. Park, S.H. Kim and S. Chang, J. Am. Chem. Soc., 130, 17268 (2008); https://doi.org/10.1021/ja808080h
  4. N. Borduas and D.A. Powell, J. Org. Chem., 73, 7822 (2008); https://doi.org/10.1021/jo801322p
  5. S. Ueda and H. Nagasawa, J. Org. Chem., 74, 4272 (2009); https://doi.org/10.1021/jo900513z
  6. Y. Gao, G. Wang, L. Chen, P. Xu, Y. Zhao, Y. Zhou and L.-B. Han, J. Am. Chem. Soc., 131, 7956 (2009); https://doi.org/10.1021/ja9023397
  7. A.E. King, T.C. Brunold and S.S. Stahl, J. Am. Chem. Soc., 131, 5044 (2009); https://doi.org/10.1021/ja9006657
  8. Y. Wei, H. Zhao, J. Kan, W. Su and M. Hong, J. Am. Chem. Soc., 132, 2522 (2010); https://doi.org/10.1021/ja910461e
  9. L. Chu and F.-L. Qing, Org. Lett., 12, 5060 (2010); https://doi.org/10.1021/ol1023135
  10. T. Uemura, S. Imoto and N. Chatani, Chem. Lett., 35, 842 (2006); https://doi.org/10.1246/cl.2006.842
  11. T.P. Lockhart, J. Am. Chem. Soc., 105, 1940 (1983); https://doi.org/10.1021/ja00345a045
  12. D.H.R. Barton, J.-P. Finet and J. Khamsi, Tetrahedron Lett., 28, 887 (1987); https://doi.org/10.1016/S0040-4039(01)81015-7
  13. D.H.R. Barton, J.-P. Finet and J. Khamsi, Tetrahedron Lett., 29, 1115 (1988); https://doi.org/10.1016/S0040-4039(00)86664-2
  14. R.J. Phipps, N.P. Grimster and M.J. Gaunt, J. Am. Chem. Soc., 130, 8172 (2008); https://doi.org/10.1021/ja801767s
  15. R.J. Phipps and M.J. Gaunt, Science, 323, 1593 (2009); https://doi.org/10.1126/science.1169975
  16. F. Besselievre, S. Piguel, Angew. Chem. Int. Ed., 48, 9553 (2009); https://doi.org/10.1002/anie.200904776
  17. J.J. Mousseau, J.A. Bull and A.B. Charette, Angew. Chem. Int. Ed., 49, 1115 (2010); https://doi.org/10.1002/anie.200906020
  18. M.Y. Min, R.J. Song, X.H. Ouyang and J.H. Li, Chem. Commun., 55, 3646 (2019); https://doi.org/10.1039/C9CC00469F
  19. J. Pan, X.Y. Li, X. Qiu, X. Luo and N. Jiao, Org. Lett., 20, 2762 (2018); https://doi.org/10.1021/acs.orglett.8b00992
  20. F. Chen, S.Q. Lai, F.F. Zhu, Q. Meng, Y. Jiang, W. Yu and B. Han, ACS Catal., 8, 8925 (2018); https://doi.org/10.1021/acscatal.8b02445
  21. D.E. McCoy, T. Feo, T.A. Harvey and R.O. Prum, Nat. Commun., 9, 1 (2018); https://doi.org/10.1038/s41467-017-02088-w
  22. B. Zhao, H.-W. Liang, J. Yang, Z. Yang and Y. Wei, ACS Catal., 7, 5612 (2017); https://doi.org/10.1021/acscatal.7b01876
  23. F. Wang D. Wang X. Wan L. Wu P. Chen and G. Liu, J. Am. Chem. Soc., 138, 15547 (2016); https://doi.org/10.1021/jacs.6b10468
  24. W. Xue, Z.W. Qu, S. Grimme and M. Oestreich, J. Am. Chem. Soc., 138, 14222 (2016); https://doi.org/10.1021/jacs.6b09596
  25. Y. Gao, Y. Gao, X. Tang, J. Peng, M. Hu, W. Wu and H. Jiang, Org. Lett., 18, 1158 (2016); https://doi.org/10.1021/acs.orglett.6b00272
  26. L. Zhou, H. Yi, L. Zhu, X. Qi, H. Jiang, C. Liu, Y. Feng, Y. Lan and A. Lei, Sci. Rep., 5, 15934 (2015); https://doi.org/10.1038/srep15934
  27. R.V. Kalla, E. Elzein, T. Perry, X. Li, V. Palle, V. Varkhedkar, A. Gimbel, T. Maa, D. Zeng and J. Zablocki, J. Med. Chem., 49, 3682 (2006); https://doi.org/10.1021/jm051268+
  28. R.-Y. Lin, B.-N. Wu, Y.-C. Lo, L.-M. An, Z.-K. Dai, Y.-T. Lin, C.-S. Tang and I.-J. Chen, J. Pharmacol. Exp. Ther., 316, 709 (2006); https://doi.org/10.1124/jpet.105.092171
  29. K. Ito, S. Lim, G. Caramori, B. Cosio, K.F. Chung, I.M. Adcock and P.J. Barnes, Proc. Natl. Acad. Sci. USA, 99, 8921 (2002); https://doi.org/10.1073/pnas.132556899
  30. Y.-C. Kim, Y. Karton, X.-D. Ji, N. Melman, J. Linden and K.A. Jacobson, Drug Dev. Res., 47, 178 (1999); https://doi.org/10.1002/(SICI)1098-2299(199908)47:4<178::AIDDDR4>3.0.CO;2-L
  31. K.A. Jacobson, A.P. Ijzerman and J. Linden, Drug Dev. Res., 47, 45 (1999); https://doi.org/10.1002/(SICI)1098-2299(199905)47:1<45::AIDDDR6>3.0.CO;2-U
  32. Y.-C. Kim, X. Ji, N. Melman, J. Linden and K.A. Jacobson, J. Med. Chem., 43, 1165 (2000); https://doi.org/10.1021/jm990421v
  33. J.W. Daly and B.B. Fredholm, Drug Alcohol Depend., 51, 199 (1998); https://doi.org/10.1016/S0376-8716(98)00077-5
  34. M. Ding, S.N. Bhupathiraju, A. Satija, R.M. van Dam and F.B. Hu, Circulation, 129, 643 (2014); https://doi.org/10.1161/CIRCULATIONAHA.113.005925
  35. K. Ker, P.J. Edwards, L.M. Felix, K. Blackhall and I. Roberts, Cochrane Database Syst. Rev., 5, CD008508 (2010); https://doi.org/10.1002/14651858.CD008508
  36. R.M. van Dam, Appl. Physiol. Nutr. Metab., 33, 1269 (2008); https://doi.org/10.1139/H08-120
  37. P. Muriel and J. Arauz, Fitoterapia, 81, 297 (2010); https://doi.org/10.1016/j.fitote.2009.10.003
  38. B. Roy, H. Rahaman, S. Hazra and B. Mondal, Synlett, 32, 1757 (2021); https://doi.org/10.1055/a-1542-9683
  39. B. Zou, Q. Yuan and D. Ma, Angew. Chem. Int. Ed., 46, 2598 (2007); https://doi.org/10.1002/anie.200700071
  40. M. Carril, R. SanMartin and E. Domínguez, Chem. Soc. Rev., 37, 639 (2008); https://doi.org/10.1039/b709565c
  41. T.R.M. Rauws and B.U.W. Maes, Chem. Soc. Rev., 41, 2463 (2012); https://doi.org/10.1039/c1cs15236j
  42. S.-J. Li and Y. Lan, Chem. Commun., 56, 6609 (2020); https://doi.org/10.1039/D0CC01946A
  43. C. Zhang and N. Jiao, J. Am. Chem. Soc., 132, 28 (2010); https://doi.org/10.1021/ja908911n
  44. J.B. Arterburn, M. Pannala and A.M. Gonzalez, Tetrahedron Lett., 42, 1475 (2001); https://doi.org/10.1016/S0040-4039(00)02315-7
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0