N,O-, N,N-, N,S- AND N,N,S-HETEROCYCLES WITH AN EXOCYCLIC AMINOGROUP IN THE SYNTHESIS OF 1,5,3,7-DIAZADIPHOSPHACYCLOOCTANES

Capa

Citar

Texto integral

Acesso aberto Acesso aberto
Acesso é fechado Acesso está concedido
Acesso é fechado Somente assinantes

Resumo

New 1,5,3,7-diazadiphosphacyclooctanes with N,O-, N,N-, N,S- and N,N,S-heterocyclic substituents at nitrogen atoms were synthesized. The influence of amines containing sp2-hybridized nitrogen atom on the ortho-position of the heterocyclic substituent on the result of a Mannich condensation of primary phosphines, paraformaldehyde and primary amines is revealed. The stabilization of intermediate acyclic products – aminomethyl(hydroxymethyl)arylphosphines and bis(aminomethyl)arylphosphines due to amino-imine tautomerism is a reason of the low yield of cyclic diphosphines on the base of above mentioned amines.

Sobre autores

Yu. Spiridonova

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences

Email: elli@iopc.ru
Russian, 420111, Kazan

I. Litvinov

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences

Email: elli@iopc.ru
Russian, 420111, Kazan

E. Musina

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences

Autor responsável pela correspondência
Email: elli@iopc.ru
Russian, 420111, Kazan

A. Karasik

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences

Email: elli@iopc.ru
Russian, 420111, Kazan

Bibliografia

  1. Lehn J.-M. // Chem. Soc. Rev. 2007. V. 36. P. 151–160. https://doi.org/10.1039/B616752G
  2. Lehn J.-M. // Top. Curr. Chem. 2012. V. 322. P. 1–32. https://doi.org/10.1007/128_2011_256
  3. Rowan S.J., Cantrill S.J., Cousins G.R.L., Sanders J.K.M., Stoddart J.F. // Angew. Chem. Int. Ed. 2002. V. 41. P. 898–952. https://doi.org/10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E
  4. Jin Y., Yu C., Denman R.J., Zhang W. // Chem. Soc. Rev. 2013. V. 42. № 16. P. 6634–6654. https://doi.org/10.1039/C3CS60044K
  5. Schaufelberger F., Timmer B.J.J., Ramström O. Principles of dynamic covalent chemistry. in: dynamic covalent chemistry: Principles, reactions, and applications. Zhang W., Jin Y. (Eds.). John Wiley & Sons Ltd., 2017. p. 1–30. https://doi.org/10.1002/9781119075738.ch1
  6. Blicke F.F. // Org. React. 2011. V. 1. № 10. P. 303–341. https://doi.org/10.1002/0471264180.or001.10
  7. Karasik A.A., Balueva A.S., Sinyashin O.G. // C. R. Chim. 2010. V. 13. № 8–9. P. 1151–1167. https://doi.org/10.1016/j.crci.2010.04.006
  8. Karasik A.A., Sinyashin O.G. Phosphorus based macrocyclic ligands: Synthesis and applications. In: Phosphorus compounds. Catalysis by metal complexes. V. 37. Peruzzini M., Gonsalvi L. (Eds.). Dordrecht: Springer. 2011. P. 375–444. https://doi.org/10.1007/978-90-481-3817-3_12
  9. Musina E.I., Fesenko T.I., Strelnik I.D., Polyancev F.M., Latypov Sh.K., Lönnecke P., Hey-Hawkins E., Karasik A.A., Sinyashin O.G. // Dalton Trans. 2015. V. 44. № 30. P. 13565–13572. https://doi.org/10.1039/C5DT01910A
  10. Musina E.I., Naumov R.N., Kanunnikov K.B., Dobry-nin A.B., Gomez-Ruiz S., Lönnecke P., Hey-Hawkins E., Karasik A.A., Sinyashin O.G. // Dalton Trans. 2018. V. 47. № 47. P. 16977–16984. https://doi.org/10.1039/C8DT03214A
  11. Karasik A.A., Musina E.I., Balueva A.S., Strelnik I.D., Sinyashin O.G. // Pure Appl. Chem. 2017. V. 89. № 3. P. 293–309. https://doi.org/10.1515/pac-2016-1022
  12. Musina E.I., Khrizanforova V.V.V., Strelnik I.D., Valitov M.I., Spiridonova Y.S., Krivolapov D.B., Litvinov I.A., Kadi-rov M.K., Lönnecke P., Hey-Hawkins E., Budnikova Y.H., Karasik A.A., Sinyashin O.G. // Chem. Eur. J. 2014. V. 20. № 11. P. 3169–3182. https://doi.org/10.1002/chem.201304234
  13. Shamsutdinova N.A., Strelnik I.D., Musina E.I., Gerasimova T.P., Katsyuba S.A., Babaev V.M., Krivolapov D.B., Litvinov I.A., Mustafina A.R., Karasik A.A., Sinya-shin O.G. // New J. Chem. 2016. V. 40. P. 9853–9861. https://doi.org/10.1039/C6NJ02277D
  14. Спиридонова Ю.С., Мусина Э.И., Даянова И.Р., Наумова О.Е., Литвинов И.А., Карасик А.А. // Журнал Общ. Химии. 2018. Т. 88. № 11. С. 1776–1781. https://doi.org/10.1134/S0044460X18110033
  15. Спиридонова Ю.С., Балуева А.С., Криволапов Д.Б., Литвинов И.А., Мусина Э.И., Карасик А.А., Синяшин О.Г. // Изв. АН. Сер. Хим. 2013. № 11. С. 2487–2494. https://doi.org/10.1007/s11172-013-0360-2
  16. Арбузов Б.А., Ерастов О.А., Хетагурова С.Ш. // Изв. АН СССР. Сер. Хим. 1979. № 4. С. 866–869. https://doi.org/10.1007/BF00923587
  17. Jackman L.M., Jen T. // J. Am. Chem. Soc. 1975. V. 97. P. 2811–2818. https://doi.org/10.1021/ja00843a033
  18. Jen T., Dienel B., Bowman H., Petta J., Hilt A., Loev B. // J. Med. Chem. 1972. V 15. P. 727–731. https://doi.org/10.1021/jm00277a008
  19. Rabinowitz J. // Helv. Chim. Acta. 1969. V. 52. P. 255–261. https://doi.org/10.1002/hlca.19690520125
  20. Toth G., Almasy A. // Org. Magn. Reson. 1982. V. 19. P. 219–221. https://doi.org/10.1002/mrc.1270190412
  21. Иванова T.M., Бурштейн K.Я., Мизрах Л.И., Васильев A.M., Гвоздецкий А.Н. // Химия гетероцикл. соед. 1989. № 7. С. 981–988. https://doi.org/10.1007/BF00472758
  22. Hasanein A.A., Senior S.A. // Int. J. Quantum. Chem. V. 111. № 15. P. 3993–4010. https://doi.org/10.1002/qua.22739
  23. Léon I., Tasinato N., Spada L., Alonso E.R., Mata S., Balbi A., Puzzarini C., Alonso J.L., Barone V. // ChemPlusChem. 2021. V. 86. P. 1374–1386. https://doi.org/10.1002/cplu.202100224
  24. Ghiviriga I., El-Gendy B.E.-D.M., Steeld P.J., Katri-tzky A.R. // Org. Biomol. Chem. 2009. V. 7. P. 4110–4119. https://doi.org/10.1039/B907577A
  25. Shugar D., Szczepaniak K. // Int. J. Quantum. Chem. 1981. V. 20. № 2. P. 573–585. https://doi.org/10.1002/qua.560200229
  26. Кормачев В.В., Федосеев М.С. Препаративная химия фосфора. Пермь: УрО РАН, 1992. С. 458.
  27. Koch T., Blaurock S., Hey-Hawkins E. // Eur. J. Inorg. Chem. 2000. № 10. P. 2167–2172. https://doi.org/10.1002/1099-0682(200010)2000:10<2167::AID-EJIC2167>3.0.CO;2-C
  28. Sheldrick G.M. // SADABS, Program for empirical X-ray absorption correction. Bruker-Nonius, 2004.
  29. APEX2 (Version 2.1), SAINTPlus, Data Reduction and Correction Program (Version 7.31A), BrukerAXS Inc., Madison, Wisconsin, USA, 2006.
  30. Sheldrick G.M. // Acta Crystallogr. Sect. A. 2015. V. 71. P. 3–8. https://doi.org/10.1107/S2053273314026370
  31. Sheldrick G.M. // Acta Crystallogr. Sect. C. 2015. V. 71. P. 3–8. https://doi.org/10.1107/S2053229614024218
  32. Spek A.L. // Acta Crystallogr. Sect. D. 2009. V. 65. P. 148–155. https://doi.org/10.1107/S090744490804362X
  33. Macrae C.F., Edgington P.R., McCabe P., Pidcock E., Shields G.P., Taylor R., Towler M., van de Streek J. // J. Appl. Cryst. 2006. V. 39. P. 453–459. https://doi.org/10.1107/S002188980600731X

Arquivos suplementares

Arquivos suplementares
Ação
1. JATS XML
Baixar
2.

Baixar (54KB)
Metadados
3.

Baixar (33KB)
Metadados
4.

Baixar (31KB)
Metadados
5.

Baixar (359KB)
Metadados

Declaração de direitos autorais © Ю.С. Спиридонова, И.А. Литвинов, Э.И. Мусина, А.А. Карасик, 2023