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A modified Biginelli reaction toward oxygen-bridged tetrahydropyrimidines fused with substituted 1,2,4-triazole ring

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Chemistry of Heterocyclic Compounds Aims and scope

A microwave-assisted Biginelli-like three-component condensation using salicylic aldehyde derivatives, acetone, and 5-substituted 3-amino-1,2,4-triazoles instead of the urea component results in the formation of oxygen-bridged tetrahydrotriazolopyrimidine derivatives (11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocines) in good yields and high purity. A plausible reaction mechanism for this transformation is discussed in details using literature and experimental data.

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The work was supported by Artvin Coruh University research project (BAP-2012.F19.02.24) and the Council of Higher Education of Turkey, Mevlana Exchange Program (MEV-2016-027).

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Authors and Affiliations

  1. Science-Technology Research and Application Center, Artvin Coruh University, 08000, Artvin, Turkey

    Mustafa K. Gümüş

  2. SSI “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine

    Mustafa K. Gümüş, Nikolay Yu. Gorobets, Yuriy V. Sedash, Valentin A. Chebanov & Sergey M. Desenko

  3. V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine

    Mustafa K. Gümüş, Valentin A. Chebanov & Sergey M. Desenko

Authors
  1. Mustafa K. Gümüş
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  2. Nikolay Yu. Gorobets
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  3. Yuriy V. Sedash
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  4. Valentin A. Chebanov
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  5. Sergey M. Desenko
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Corresponding author

Correspondence to Mustafa K. Gümüş.

Additional information

Supplementary information file containing 1H and 13C NMR spectral data of the obtained compounds 11a–w is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(11), 1261–1267

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Gümüş, M.K., Gorobets, N.Y., Sedash, Y.V. et al. A modified Biginelli reaction toward oxygen-bridged tetrahydropyrimidines fused with substituted 1,2,4-triazole ring. Chem Heterocycl Comp 53, 1261–1267 (2017). https://doi.org/10.1007/s10593-018-2204-3

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  • DOI: https://doi.org/10.1007/s10593-018-2204-3

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