Reaction of chloroethynylphosphonates with 1,3-diethyl 2-(acylamino)propanedioates

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription Access

Abstract

Reaction of 2-(acylamino)malonic acids esters with chloroethynylphosphonates yielded 2-substituted (5 E / Z )-5-(dialkoxyphosphoryl)methylidene-2-oxazoline-4,4-dicarboxylates, isomers of which could be separated. Following reaction of hydrolysis and decarboxylation affords 2-substituted 5-(dialkoxyphosphoryl)methyl-1,3-oxazole-4-carboxylates.

About the authors

N. B. Viktorov

St. Petersburg State Institute of Technology (Technical University)

Email: kolki@mail.ru

A. V. Dogadina

St. Petersburg State Institute of Technology (Technical University)

A. V. Stepakov

St. Petersburg State Institute of Technology (Technical University);St. Petersburg University

References

  1. Yeh V., Iyengar R. // Compr. Heterocycl. Chem. III. 2008. Vol. 4. P. 487. doi: 10.1016/b978-008044992-0.00404-1
  2. Gant T.G, Meyers A.I. // Tetrahedron. 1994. Vol. 50. N 8. P. 2297. doi: 10.1016/S0040-4020(01)86953-2
  3. McManus H.A., Guiry P.J. // Chem. Rev. 2004. Vol. 104. N 9. P. 4151. doi: 10.1021/cr040642v
  4. Hargaden G.C., Guiry P.J. // Chem. Rev. 2009. Vol. 109. N 6. P. 2505. doi: 10.1021/cr800400z
  5. Kakkar S., Narasimhan B. // BMC Chem. 2019. Vol. 13. Article 16. doi: 10.1186/s13065-019-0531-9
  6. Abdurakhmanova E.R., Brusnakov M.Y., Golovchenko O.V., Pilyo S.G., Velychko N.V., Harden E.A., Prichard M.N., James S.H., Zhirnov V.V., Brovarets V.S. // Med. Chem. Res. 2020. Vol. 29. P. 1669. doi: 10.1007/s00044-020-02593-6
  7. Храмчихин В.А., Догадина А.В., Храмчихин А.В., Ионин Б.И. // ЖОХ. 2012. Т. 82. Вып. 4. С. 694
  8. Khramchikhin V.A., Dogadina A.V., Khramchikhin A.V., Ionin B.I. // Russ. J. Gen. Chem. 2012. Vol. 82. N 4. P. 776. doi: 10.1134/S1070363212040299
  9. Seitz Th., Baudoux J., Bekolo H., Cahard D., Plaquevent J.Ch., Lasne M.C., Rouden J. // Tetrahedron. 2006. Vol. 62. N 26. P. 6155. doi: 10.1016/j.tet.2006.04.062
  10. Varano F., Catarzi D., Squarcialupi L., Betti M., Vincenzi F., Ravani A., Varani K., Ben D., Thomas A., Volpini R., Colotta V. // Eur. J. Med. Chem. 2015. Vol. 96. N 26. P. 105. doi: 10.1016/j.ejmech.2015.04.010

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2023 Russian Academy of Sciences