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Synthesis of podands with dihydropyrimidine fragments based on polyethers with terminal acetoacetamide groups

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Chemistry of Heterocyclic Compounds Aims and scope

Reactions of aliphatic aminopodands having different length of the polyether chain with acetoacetic ester and 2,2,6-trimethyl-4H-1,3-dioxin-4-one 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 byproduct from the reaction of dioxinone with 1,5-diamino-3-oxapentane. A three-component Biginelli reaction of acetoacetamidecontaining 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.

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The authors are grateful to Professor A. N. Murashkevich (Belarus State Technological University) for the provided samples of nanosized oxides.

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 Mira St., Yekaterinburg, 620002, Russia

    Elena S. Radionova, Olga V. Fedorova, Yulia A. Titova, Gennady L. Rusinov & Valery N. Charushin

  2. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 S. Kovalevskoi / Akademicheskaya St., Yekaterinburg, 620990, Russia

    Elena S. Radionova, Olga V. Fedorova, Yulia A. Titova, Gennady L. Rusinov & Valery N. Charushin

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  1. Elena S. Radionova
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  2. Olga V. Fedorova
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  3. Yulia A. Titova
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  4. Gennady L. Rusinov
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  5. Valery N. Charushin
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Correspondence to Elena S. Radionova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(5), 478–482

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Radionova, E.S., Fedorova, O.V., Titova, Y.A. et al. Synthesis of podands with dihydropyrimidine fragments based on polyethers with terminal acetoacetamide groups. Chem Heterocycl Comp 51, 478–482 (2015). https://doi.org/10.1007/s10593-015-1723-4

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  • DOI: https://doi.org/10.1007/s10593-015-1723-4

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