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Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol

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Abstract

(S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol was synthesized in two steps by the Diels-Alder reaction of penta-2,4-dien-1-ol with diethyl azodicarboxylate in the presence of (S)-BINOL as chiral catalyst. The subsequent Boc-protection of the 2-position of the pyridazine ring, ring-closing carbonylation of the hydroxy group, and deprotection afforded a bicyclic iminosugar analog. The structure of the isolated compounds was proved by NMR, IR, and mass spectra and elemental analyses.

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Authors and Affiliations

  1. Baku State University, Baku, 1148, Azerbaijan

    F. N. Axundova, M. M. Kurbanova & A. E. Huseynzada

  2. Universidade do Minho de Gualtar, Braga, 4710-057, Portugal

    M. J. Alves

Authors
  1. F. N. Axundova
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  2. M. M. Kurbanova
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  3. A. E. Huseynzada
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  4. M. J. Alves
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Corresponding author

Correspondence to F. N. Axundova.

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Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 12, pp. 1942–1946.

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Axundova, F.N., Kurbanova, M.M., Huseynzada, A.E. et al. Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol. Russ J Org Chem 55, 1975–1978 (2019). https://doi.org/10.1134/S1070428019120297

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  • DOI: https://doi.org/10.1134/S1070428019120297

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