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New transformations of N-hetarylcyclopentano[d][1,2,3]triazoline ring into 5-alkoxyvaleramidines

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Chemistry of Heterocyclic Compounds Aims and scope

It was found that brief refluxing of N-hetarylcyclopentano[d][1,2,3]triazolines in methanol resulted in the elimination of nitrogen, accompanied by cyclopentane ring opening with the formation of N-hetarylvaleramidines. Amidines containing pyrimidine-2,4-dione ring were synthesized by a one-step procedure – the reaction of 5-azidopyrimidine-2,4-diones with endocyclic enamines containing a cyclopentene ring proceeded through an N-pyrimidyl-1,2,3-triazoline intermediate. Triazolines containing a 1,3,5-triazine ring at position 1 did not form valeramidines upon refluxing in methanol. N-(1,3,5-triazin-2-yl)cyclopenta[d][1,2,3]triazoline containing a morpholine ring at position 6a underwent a different type of transformation upon dissolving in acetic acid, resulting in the formation of N-(1,3,5-triazin-2-yl)diaminoalkene. Mechanisms for these transformations are proposed.

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This work was performed with financial support from the Russian Foundation for Basic Research (grant No. 18-03-00715).

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Authors and Affiliations

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

    Nikolay A. Belyaev, Tetyana V. Beryozkina & Vasiliy A. Bakulev

  2. Department of Neuroproteomics, Paracelsus Medical University, 5020, Salzburg, Austria

    Gert Lubec

  3. Laboratory of Molecular Design and Synthesis, Department of Chemistry, Catholic University of Leuven, 3001, Leuven, Belgium

    Wim Dehaen

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  1. Nikolay A. Belyaev
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  5. Vasiliy A. Bakulev
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Correspondence to Vasiliy A. Bakulev.

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Belyaev, N.A., Beryozkina, T.V., Lubec, G. et al. New transformations of N-hetarylcyclopentano[d][1,2,3]triazoline ring into 5-alkoxyvaleramidines. Chem Heterocycl Comp 54, 1050–1055 (2018). https://doi.org/10.1007/s10593-018-2390-z

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