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New Molecular Scaffolds Based on 2,8-Xylylene-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione

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Abstract

A series of novel glycouril derivatives were synthesized through Mannich condensation of 2,8-xylylene-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione with formaldehyde and alkylamines or diamines. These glycoluril derivatives may be regarded as molecular scaffolds acting as excellent receptors.

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REFERENCES

  1. Rheineck, H., Justus Liebigs Ann. Chem., 1865, vol. 134, p. 219. https://doi.org/10.1002/jlac.18651340209

    Article  Google Scholar 

  2. Schiff, H., Justus Liebigs Ann. Chem., 1877, vol. 189, p. 157. https://doi.org/10.1002/jlac.18771890110

    Article  Google Scholar 

  3. Slezak, F., Hirsch, A., and Rosen, I., J. Org. Chem., 1960, vol. 25, p. 660. https://doi.org/10.1021/jo01074a619

    Article  CAS  Google Scholar 

  4. Kang, J., In, S., and Cho, S.J., Supramol. Chem., 2007, vol. 19, p. 243. https://doi.org/10.1080/10610270701358491

    Article  CAS  Google Scholar 

  5. Smeets, J.W.H., Sijbesma, R.P., Niele, F.G.M., Spek, A.L., Smeets, W.J.J., and Nolte, R.J.M., J. Am. Chem. Soc., 1987, vol. 109, p. 928. https://doi.org/10.1021/ja00237a064

    Article  CAS  Google Scholar 

  6. Ghosh, S., Wu, A., Fettinger, J.C., Zavalij, P.Y., and Isaacs, L., J. Org. Chem., 2008, vol. 73, p. 5915. https://doi.org/10.1021/jo8009424

    Article  CAS  Google Scholar 

  7. Wu, A., Mukhopadhyay, P., Chakraborty, A., Fet­tinger, J.C., and Isaacs, L., J. Am. Chem. Soc., 2004, vol. 126, p. 10035. https://doi.org/10.1021/ja0486972

    Article  CAS  Google Scholar 

  8. Smeets, J.W.H., Sijbesma, R.P., Dalen, L.V., Spek, A.L., Smeets, W.J.J., and Nolte, R.J.M., J. Org. Chem., 1989, vol. 54, p. 3710. https://doi.org/10.1021/jo00276a037

    Article  CAS  Google Scholar 

  9. Sanderson, P.E.J., Kilburn, J.D., and Still, W.C., J. Am. Chem. Soc., 1989, vol. 111, p. 8314. https://doi.org/10.1021/ja00203a062

    Article  CAS  Google Scholar 

  10. Conn, M.M. and Rebek Jr, J., Chem. Rev., 1997, vol. 97, p. 1647. https://doi.org/10.1021/cr9603800

    Article  CAS  Google Scholar 

  11. Rebek Jr, J., Acc. Chem. Res., 1999, vol. 32, p. 278. https://doi.org/10.1021/ar970201g

    Article  Google Scholar 

  12. Hof, F., Craig, S.L., Nuckolls, C., and Rebek Jr, J., Angew. Chem., Int. Ed., 2002, vol. 41, p. 1488. https://doi.org/10.1002/1521-3773(20020503)41:9<1488::AID-ANIE1488>3.0.CO;2-G

    Article  CAS  Google Scholar 

  13. Freeman, W.A., Mock, W.L., and Shih, N.Y., J. Am. Chem. Soc., 1981, vol. 103, p. 7367. https://doi.org/10.1021/ja00414a070

    Article  CAS  Google Scholar 

  14. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., and Isaacs, L., Angew. Chem., Int. Ed., 2005, vol. 44, p. 4844. https://doi.org/10.1002/anie.200460675

    Article  CAS  Google Scholar 

  15. Ni, X., Xiao, X., Cong, H., Zhu, Q., Xue, S., and Tao, Z., Acc. Chem. Res., 2014, vol. 47, p. 1386. https://doi.org/10.1021/ar5000133

    Article  CAS  Google Scholar 

  16. Kim, J., Jung, I., Kim, S., Lee, E., Kang, J., Saka­moto, S., Yamaguchi, K., and Kim, K., J. Am. Chem. Soc., 2000, vol. 122, p. 540. https://doi.org/10.1021/ja993376p

    Article  CAS  Google Scholar 

  17. Day, A.I., Blanch, R.J., Arnold, A.P., Lorenzo, S., Lewis, G.R., and Dance, I., Angew. Chem., Int. Ed., 2002, vol. 41, p. 275. https://doi.org/10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M

    Article  CAS  Google Scholar 

  18. Reek, J.N.H., Priem, A.H., Engelkamp, H., Rowan, A.E., Elemans, J.A.A.W., and Nolte, R.J.M., J. Am. Chem. Soc., 1997, vol. 119, p. 9956. https://doi.org/10.1021/ja970805f

    Article  CAS  Google Scholar 

  19. Thordarson, P., Bijsterveld, E.J.A., Elemans, J.A.A.W., Kasák, P., Nolte, R.J.M., and Rowan, A.E., J. Am. Chem. Soc., 2003, vol. 125, p. 1186. https://doi.org/10.1021/ja028463n

    Article  CAS  Google Scholar 

  20. Kang, J., Jo, J., and In, S., Tetrahedron Lett., 2004, vol. 45, p. 5225. https://doi.org/10.1016/j.tetlet.2004.05.040

    Article  CAS  Google Scholar 

  21. Kim, H., In, S., and Kang, J., Supramol. Chem., 2006, vol. 18, p. 141. https://doi.org/10.1080/10610270600564702

    Article  CAS  Google Scholar 

  22. Stancl, M., Necas, M., Taraba, J., and Sindelar, V., J. Org. Chem., 2008, vol. 73, p. 4671. https://doi.org/10.1021/jo800699s

    Article  CAS  Google Scholar 

  23. Ma, Z., Gargulakova, Z., Zavalij, P.Y., Sindelar, V., and Isaacs, L., J. Org. Chem., 2010, vol. 75, p. 2934. https://doi.org/10.1021/jo100186q

    Article  CAS  Google Scholar 

  24. Stancl, M., Gilberg, L., Ustrnul, L., Necas, M., and Sindelar, V., Supramol. Chem., 2014, vol. 26, p. 168. https://doi.org/10.1080/10610278.2013.842643

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Hubei Key Laboratory of Mine Environmental Pollution Control & Remediation, School of Chemistry and Chemical Engineering, HuBei Polytechnic University, 435003, Huangshi, China

    Zhi-Guo Wang

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  1. Zhi-Guo Wang
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Correspondence to Zhi-Guo Wang.

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Wang, ZG. New Molecular Scaffolds Based on 2,8-Xylylene-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione. Russ J Org Chem 58, 1451–1454 (2022). https://doi.org/10.1134/S1070428022100104

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  • DOI: https://doi.org/10.1134/S1070428022100104

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