A New Method for the Synthesis of N-Monosubstituted 1,3-Diaminopropanes

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Abstract

A new method for the synthesis of N-monosubstituted diamines has been developed. On the first step 1,3-diaminopropane is protected with phthalic anhydride to form a heterocyclic system - 3,4-dihydropyrimidino[2,1-a]isoindol-6(2H)-one, which is then subjected to selective alkylation followed by removal of the protective phthalyl group, that leads to the target diamines with a total yield of up to 66% without formation of excessively alkylated diaminopropanes. The paper presents the X-ray data of new compounds - 1-methyl-6-oxo-2,3,4,6-tetrahydropyrimido[2,1-a]isoindol-1-ium iodide and 3-(1,3-dioxoisoindoline-2-yl)-N-methylpropan-1-aminium iodide.

About the authors

G. S Martyanov

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0009-0000-1152-0317
Ekaterinburg, Russia

M. A Barabanov

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0002-5850-8443
Ekaterinburg, Russia

A. R Gindullin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal University named after the First President of Russia B.N. Yeltsin

ORCID iD: 0009-0000-2916-1850
Ekaterinburg, Russia; Ekaterinburg, Russia

P. A Slepukhin

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences

ORCID iD: 0000-0001-8132-9905
Ekaterinburg, Russia

A. V Pestov

Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences; Ural Federal University named after the First President of Russia B.N. Yeltsin

Email: flimsey@mail.ru
ORCID iD: /0000-0002-4270-3041
Ekaterinburg, Russia; Ekaterinburg, Russia

References

  1. Morton D.R., US Patent no. 3920565, 1975. https://patents.google.com/patent/US3920565A/en?oq=US3920565A
  2. Schilling P., US Patent no. 6077888, 2000. https://patents.google.com/patent/US6077888A/en?oq=US6077888A
  3. Shortis J., EP Patent no. 1511828, 2005. https://patents.google.com/patent/EP1511828A1/de?oq=EP1511828A1
  4. Michailovski A., Budemberg G., Sobotka B., Kierat R., EP Patent no. 4196281, 2023. https://patents.google.com/patent/EP4196281A1/en
  5. Sonderman B., Buschmann H., Kogel B.-Y., Murra B., Risch N., CN Patent no. 100434421, 2008. https://patents.google.com/patent/CN100434421C/en?oq=CN100434421C
  6. Fujimoto N., Poly(ethylene glycol)-conjugated Alkylamines as Novel Blocking Reagents for Immunoassays, 2009. https://ediss.sub.uni-hamburg.de/bitstream/ediss/2659/1/Dissertation_NahoFujimoto.pdf
  7. Tamano Y., Kometani H., Ishida M., EP Patent no. 1092737, 2001. https://patents.google.com/patent/EP1092737A3/en
  8. Chao Zh., Yang Zh., Xi L., Chengli F., CN Patent no. 113647390, 2021. https://patents.google.com/patent/CN113647390A/en?oq=CN113647390
  9. Dong S., Fan J., Hongmiao L., Qiang T., Ji Y., Han W., Journal of Surfactants and Detergents, 2023, 27, 135–145. https://doi.org/10.1002/jsde.12709
  10. Wang L.-Ch., Chen B., Wu X.-F., Angewandte Chemie International Edition, 2022, 61, 37–53. https://doi.org/10.1002/anie.202203797
  11. Reis R.C.N., Oda S.C., De Almeida M.V., Lourenço M.C.S, Vicente F.R.C., Barbosa N.R., Trevizani R., Santosc P.L.C, Hyaric M., J. Braz. Chem. Soc., 2008, 19, 1065–1072. https://doi.org/10.1590/S0103-50532008000600003
  12. Decroos C., Bowman C.M., Christianson D.W., Bioorganic & Medicinal Chemistry, 2013, 21, 4530–4540. https://doi.org/10.1016/j.bmc.2013.05.045
  13. Giordani R.B., De Almeida M.V., Fernandes E., França da Costa C., De Carli G.A., Tasca T., Zuanazzi J.A.S., Biomedicine & Pharmacotherapy, 2009, 63, 613–617. https://doi.org/10.1016/j.biopha.2008.10.002
  14. da Costa C.F., Coimbra E.S., Braga F.G., dos Reis R.C.N., da Silva D., de Almeida M.V., Biomedicine & Pharmacotherapy, 2009, 63, 40–42. https://doi.org/10.1016/j.biopha.2007.12.013
  15. Silva H., Barra C.V., da Costa C.F., de Almeida M.V., César E.T., Silveira J.N., Garnier-Suillerot A., de Paula F.C.S., Pereira-Maia E.C., Fontes A.P.S., Journal of Inorganic Biochemistry, 2008, 102, 767–772. https://doi.org/10.1016/j.jinorgbio.2007.11.013
  16. Bergmann D.J., Campi E.M., Jackson W.R., Patti A.F., Australian Journal of Chemistry, 1999, 52, 1131–1138. https://doi.org/10.1071/CH99097
  17. Farzaliev V.M., Babaeva G.B., Abbasova M.T., Nabiev O.G., Soltanova Z.K., Kerimova Ya.M., Chemistry and Technology of Fuels and Oils, 2000, 45, 98–102. https://link.springer.com/article/10.1007/s10553-009-0104-z
  18. Kabalka G.W., Wang Z., Synthetic Communications, 1990, 20, 2113–2118. https://doi.org/10.1080/00397919008053146
  19. Vedage G.A., Raymond W.R.E., O'Conell E.M., Foo M.L., Lucas P.A., EP Patent no. 2157113, 2011. https://patents.google.com/patent/EP2157113B1/de?oq=EP2157113B1
  20. Häkkinen M.R., Keinänen T.A., Khomutov A.R., Auriola S., Weisell J., Alhonen L., Jänne J., Vepsäläinen J., Tetrahedron, 2009, 65, 547–562. https://doi.org/10.1016/j.tet.2008.10.071
  21. Dechambenoit P., Ferlay S., Kyritsakas N., Hosseini M.W., New Journal of Chemistry, 2010, 1184–1199. https://doi.org/10.1039/b9nj00625g
  22. Мартьянов Г.С., Барабанов М.А., Пестов А.В., ЖОрХ, 2025, в печати.
  23. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H., Journal of Applied Crystallography, 2009, 42, 339–341. https://doi.org/10.1107/S0021889808042726
  24. Sheldrick G.M., Acta Cryst., 2008, A64, 112–122. https://doi.org/10.1107/S0108767307043930
  25. Faust J.A., Sahyun M., US Patent no. 2953565, 1956. https://patents.google.com/patent/US2953565A/en?oq=US2953565
  26. Weitzel G., Pfeiffer B., Stock W., Hoppe-Seyler´s Zeitschrift Für Physiologische Chemie, 1980, 361, 51–60. https://doi.org/10.1515/bchm2.1980.361.1.51

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