Synthesis of Cyclobutaquinoxaline-1,2-diol Derivatives from 1,2-dihydroxy-3,4- Cyclobutendiones

Document Type : Original Article

Authors

1 Department of Chemistry, Faculty of Science, Vali-e-Asr University of Rafsanjan

2 Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan

3 Payam-e Noor University of Kerman

Abstract

Among the various classes of nitrogen-containing heterocyclic compounds, quinoxalines play an important role as a basic skeleton for the design of a number of antibiotics. In addition, quinoxaline ring is a part of several pharmacological active substances of natural or synthetic origin. In this study, an ecofriendly method for the synthesis of cyclobutaquinoxaline-1,2-diol derivatives through cycloaddition reaction of O-phenylenediamine derivatives and squaric acid in EtOH as a green solvent in the presence of a catalytic amount of acetic acid under reflux condition is reported. Different diamine compounds such as 4-methylbenzene-1,2-diamine, 4-chlorobenzene-1,2-diamine, 4-nitrobenzene-1,2-diamine and pyridine-2,3-diamine were used. The structures of products were confirmed by FT-IR, 1H-NMR, 13C-NMR, and elemental analysis.the reaction of 2,3-diaminopyridine with squaric acid give the corresponding cyclobuta[e]pyrido[3,2-b]pyrazine-6,7-diol. According to the spectroscopic data (FT-IR and H-NMR data) in this reaction there might be three isomers in the cyclobuta[e]pyrido[3,2-b]pyrazine-6,7-diol. These isomers are tautomers. In summary, we have developed a new facile and ecofriendly protocol for the synthesis cyclobutaquinoxaline-1,2-diol derivatives from reaction of O-phenylenediamine derivatives and squaric acid.

Graphical Abstract

Synthesis of Cyclobutaquinoxaline-1,2-diol Derivatives from 1,2-dihydroxy-3,4- Cyclobutendiones

Keywords

References

1) C. W Lee, H. Cao, K. Ichiyama, T. M. Rana, Bioorg. Med. Chem. Lett., 15, 424 (2005).
2) G. Lai, J. R. Merritt, Zh. He, D.Feng, J. Chao, M. F. Czarniecki, L. L. Rokosz, T. M. Stauffer,  D. Rindgen, A. G. Taveras, Bioorg. Med. Chem. Lett., 18, 1864 (2008).
3) C. S. Cho, S. G. Oh, J. Mol. Catal. A: Chem., 276, 205 )2007(.
4) R. U. Braun, T. J. J. Muller, Synthesis, 2391 (2004).
5) C.S. Cho, B.T. Kim, T. J. Kim, S.C.Shim, Tetrahedron. Lett., 43, 7987 (2002).
6) A. Dell, D. H. William, H. R. Morris, G. A. Smith, J. Feeney, J.C. K. Roberts, J. Am. Chem. Soc, 97, 2497 (1975).
7) L. S. Jonathan, M. Hiromitsu, M. Toshihisa, M. L. Vincent, F. Hiroyuki, Chem. Commun., 862 (2002).
8) D. Gupta, N. N. Ghosh, R. Chandra, Bioorg. Med. Chem. Lett., 15, 1019 (2005).
9) M. A. Naylor, M. A. Stephen, J. Nolan, B. Sutton, J. H. Tocher, E. M. Fielden, G. E. Adams,  I. J. Strafford, Anti-Cancer Drug Des., 8, 439 (1993).
10) G. Sakata, K. Makino, Y. Kuraswa, Heterocycles, 27, 2481 (1988).
11) A. Shaabani, F. Hajishaabanha, M. Mahyari, H. Mofakhama, S. Weng Ng. Tetrahedron., 67, 8360 (2011).
Iranian Journal of Chemistry
Volume 2, Issue 1 - Serial Number 2
September 2019
Pages 65-69

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History

  • Receive Date: 23 November 2018
  • Revise Date: 18 January 2019
  • Accept Date: 11 October 2019

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