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Features of a multicomponent Biginelli reaction involving 3-oxobutanoyl-containing podands, aromatic aldehydes, and 1,2,4-triazol-3-amine

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Chemistry of Heterocyclic Compounds Aims and scope

A reaction of 3-oxobutanoyl-containing podands with thiophene-2-carbaldehyde (or benzaldehyde) and 3-amino-1,2,4-triazole gave podands featuring a 4,7-dihydro[1,2,4]triazolo[1,5-а]pyrimidine motif. It was established that the process was accompanied by the formation of [4,3-а]-isomers, which occurred in a slight excess during the synthesis of a podand containing a phenyl group at position 7 and, on the other hand, were observed as the minor products during the synthesis of podands bearing a thiophen-2-yl substituent. Trace amounts of monosubstituted podands were also detected, containing a free hydroxy group along with the triazolodihydropyrimidine pharmacophore.

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Authors and Affiliations

  1. Postovsky Institute of Organic Synthesis, Ural branch of the Russian Academy of Sciences, 22 S. Kovalevskoi / 20 Akademicheskaya St, Yekaterinburg, 620990, Russia

    Elena S. Filatova, Olga V. Fedorova, Konstantin A. Chistyakov, Gennady L. Rusinov & Valery N. Charushin

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

    Gennady L. Rusinov & Valery N. Charushin

Authors
  1. Elena S. Filatova
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  2. Olga V. Fedorova
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  3. Konstantin A. Chistyakov
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  4. Gennady L. Rusinov
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  5. Valery N. Charushin
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Corresponding author

Correspondence to Elena S. Filatova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 88–91

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Filatova, E.S., Fedorova, O.V., Chistyakov, K.A. et al. Features of a multicomponent Biginelli reaction involving 3-oxobutanoyl-containing podands, aromatic aldehydes, and 1,2,4-triazol-3-amine. Chem Heterocycl Comp 56, 88–91 (2020). https://doi.org/10.1007/s10593-020-02627-2

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  • DOI: https://doi.org/10.1007/s10593-020-02627-2

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