SYNTHESIS OF PODANDS WITH DIHYDROPYRIMIDINE FRAGMENTS BASED ON POLYETHERS WITH TERMINAL ACETOACETAMIDE GROUPS

Authors

  • Елена С. Радионова Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia . Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg 620990, Russia
  • Ольга B. Федорова Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia . Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg 620990, Russia
  • Юлия A. Титова Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia . Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg 620990, Russia
  • Геннадий Л. Русинов Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia . Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg 620990, Russia
  • Валерий H. Чарушин Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia . Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg 620990, Russia

DOI:

https://doi.org/10.1007/2243

Keywords:

acetoacetamide-containing podands, acetylketene, dihydropyrimidine-containing podands, nanosized oxide, polyphosphoric acid, Biginelli reaction

Abstract

Reactions of aliphatic aminopodands having different length of the polyether chain with acetoacetic ester and 2,2,6-trimethyl-4H1,3-dioxin-4one were studied. The interaction of aminopodands with acetoacetic ester in toluene upon sonication (60°С) or heating (90°С) gave podands with terminal aminocrotonate fragments. The use of dioxinone at the same temperature allowed to transform aminopodands into aliphatic acetoacetamide-containing podands. An asymmetric podand with 2-pyridone fragment was isolated as by-product from the reaction of dioxinone with 1,5-diamino-3-oxapentane. A three-component Biginelli reaction of acetoacetamide-containing podands with benzaldehyde and urea in the presence of catalytic amounts of polyphosphoric acid immobilized on nanosized TiO2–SiO2 oxide surface enabled the synthesis of podands with 1,4-dihydropyrimidin-2-(1Н)-one fragments.

How to Cite
Radionova, E. S.; Fedorova, O. V.; Titova, Yu. A.; Rusinov, G. L.; Charushin, V. N. Chem. Heterocycl. Compd. 2015, 51, 478. [Khim. Geterotsikl. Soedin. 2015, 51, 478.]

For this article in the English edition see DOI 10.1007/s10593-015-1723-4

 

 

Author Biography

Елена С. Радионова, Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg 620002, Russia . Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg 620990, Russia

Елена Сергеевна Радионова

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Published

2015-05-17

Issue

Vol. 51 No. 5 (2015)

Section

Original Papers