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Phosphorylation of Betti Base with Bis(diethylamino)phosphoryl Chloride

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Abstract

The reaction of bis(diethylamino)phosphoryl chloride with N-Boc-protected 1-(α-aminobenzyl)-2- naphthol (Betti base) proceeded via O-phosphorylation of the phenolic OH group to form the target product as trifluoroacetate salt. The latter reacted with O,O-diethyl thiophosphorylisothiocyanate to give thiourea bearing a chiral Betti base fragment.

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References

  1. Zhang, J. and Li, W., Chem. Soc. Rev., 2016, vol. 45, p. 1657. doi 10.1039/c5cs00469a

    Article  PubMed  Google Scholar 

  2. Chen, X.-S., Hou, C.-J., and Hu, X.-P., Synth. Commun., 2016, vol. 46, no. 11, p. 917. doi 10.1080/00397911.2016.1171362

    Article  CAS  Google Scholar 

  3. Terada, M., Synthesis, 2010, no. 12, p. 1929. doi 10.1055/s-0029-1218801

    Article  CAS  Google Scholar 

  4. Amino Acids, Peptides and Proteins in Organic Chemistry, Hughes, A.B., Ed., Weinheim: Wiley-VCH Verlag GmbH, 2009, vol. 2, p.189.

  5. Mikolajczyk, M. and Balczewski, P., Top. Curr. Chem., 2003, vol. 223, p. 161. doi 10.1007/3-540-46100-0

    Article  CAS  Google Scholar 

  6. Nikitina, K.A., Metlushka, K.E., Sadkova, D.N., Shaimardanova, L.N., and Alfonsov, V.A., Mendeleev Commun., 2016, vol. 26, p. 395. doi 10.1016/j.mencom.2016.09.009

    Article  CAS  Google Scholar 

  7. Metlushka, K.E., Sadkova, D.N., Nikitina, K.A., Shaimardanova, L.N., Kataeva, O.N., and Alfonsov, V.A., Russ. J. Gen. Chem., 2016, vol. 86, no. 3, p. 515. doi 10.1134/S107036321603004X

    Article  CAS  Google Scholar 

  8. Metlushka, K.E., Sadkova, D.N., Shaimardanova, L.N., Nikitina, K.A., Tufatullin, A.I., Kataeva, O.N., and Alfonsov V.A., Russ. Chem. Bull., 2014, no. 6, p. 1390. doi 10.1007/s11172-014-0608-5

    Article  CAS  Google Scholar 

  9. Metlushka, K.E., Kashemirov, B.A., Zheltukhin, V.F., Sadkova, D.N., Büchner, B., Hess, C., Kataeva, O.N., McKenna, Ch.E., and Alfonsov, V.A., Chem. Eur. J., 2009, vol. 15, no. 27, p. 6718. doi 10.1002/chem.200802540

    Article  CAS  PubMed  Google Scholar 

  10. Bruker. APEX3 Crystallography Software Suite, Bruker AXS, Inc., Madison, USA, 2016.

  11. Bruker. SAINT. Crystallography Software Suite, Bruker AXS, Inc., Madison, USA, 2016.

  12. Krause, L., Herbst-Irmer, R., Sheldrick, G.M., and Stalke, D., J. Appl. Crystallogr., 2015, vol. 48, p. 3. doi 10.1107/S1600576714022985

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Sheldrick, G.M., Acta Crystallogr. (A), 2008, vol. 64, no. 1, p. 112. doi 10.1107/S0108767307043930

    Article  CAS  Google Scholar 

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Correspondence to V. A. Alfonsov.

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Dedicated to the 115th anniversary of B.A. Arbuzov’s birth

Original Russian Text © K.E. Metlushka, D.N. Sadkova, K.A. Nikitina, Z.R. Yamaleeva, K.A. Ivshin, O.N. Kataeva, V.A. Alfonsov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 11, pp. 1931–1934.

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Metlushka, K.E., Sadkova, D.N., Nikitina, K.A. et al. Phosphorylation of Betti Base with Bis(diethylamino)phosphoryl Chloride. Russ J Gen Chem 88, 2453–2456 (2018). https://doi.org/10.1134/S1070363218110348

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