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Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective сyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides

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Chemistry of Heterocyclic Compounds Aims and scope

Unusual reaction proceeding via the electrophilic activation of nitroalkanes in the presence of polyphosphoric acid has been discovered. Subsequent nucleophilic attack with semicarbazides or thiosemicarbazides allows to access 2-amino-1,3,4-oxadiazoles and 2-amino-1,3,4-thiadiazoles, respectively.

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This work was supported by the Russian Foundation for Basic Research (grant 18-33-20021 mol_a_ved, 20-33-90026).

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Authors and Affiliations

  1. Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol, 355017, Russia

    Nicolai A. Aksenov, Nikolai A. Arutiunov, Nikita K. Kirillov, Dmitrii A. Aksenov, Alexander V. Aksenov & Michael Rubin

  2. Department of Chemistry, University of Kansas, 1567 Irving Hill Rd., Lawrence, KS, 66045-7582, USA

    Michael Rubin

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  1. Nicolai A. Aksenov
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  2. Nikolai A. Arutiunov
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  3. Nikita K. Kirillov
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  4. Dmitrii A. Aksenov
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Correspondence to Nicolai A. Aksenov or Michael Rubin.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 1067–1072

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Aksenov, N.A., Arutiunov, N.A., Kirillov, N.K. et al. Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective сyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides. Chem Heterocycl Comp 56, 1067–1072 (2020). https://doi.org/10.1007/s10593-020-02775-5

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