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Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin

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Abstract

Aldol-crotonic condensation of allobetulone and betulonic aldehyde with N-substituted pyrrole-2- and pyrazole-4-carbaldehydes afforded a series of new α,β-unsaturated ketones of lupane series. Their reduction provided 2-ylidene derivatives of allobetulin and betulin, potential chiral components of liquid crystal materials. Structures of 1-phenyl-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbaldehyde, (E)-2-{[3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulone, (E)-2-{[3-(4-bromophenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}-3-oxolup-20(29)-ene-28-carbaldehyde, (E)-2-{[3-(4-bromo-phenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}allobetulin, and (E)-2-{[3-(4-bromophe-nyl)-1-phenyl-1H-pyrazol-4-yl]-methylidene}lup-20(29)-ene-3,28-diol were established by X-ray diffraction (XRD) study.

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Authors and Affiliations

  1. Institute of Single Crystals, National Academy of Sciences of Ukraine, pr. Lenina 60, Kharkiv, 61001, Ukraine

    N. L. Babak, A. N. Semenenko, I. M. Gella, V. I. Musatov, S. V. Shishkina, N. B. Novikova, D. S. Sofronov & V. V. Lipson

  2. Danilevskii Institute of Problems of Endocrine Pathology, National Academy of Medical Sciences of Ukraine, Kharkiv, Ukraine

    V. V. Lipson

  3. Karazin Kharkiv National University, Kharkiv, Ukraine

    I. M. Gella, D. A. Morina & V. V. Lipson

Authors
  1. N. L. Babak
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  2. A. N. Semenenko
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  3. I. M. Gella
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  4. V. I. Musatov
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  5. S. V. Shishkina
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  6. N. B. Novikova
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  7. D. S. Sofronov
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  8. D. A. Morina
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  9. V. V. Lipson
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Corresponding author

Correspondence to V. V. Lipson.

Additional information

Original Russian Text © N.L. Babak, A.N. Semenenko, I.M. Gella, V.I. Musatov, S.V. Shishkina, N.B. Novikova, D.S. Sofronov, D.A. Morina, V.V. Lipson, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 731–742.

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Babak, N.L., Semenenko, A.N., Gella, I.M. et al. Synthesis of pyrrol-2-yl- and pyrazol-4-ylmethylidene derivatives of betulin and allobetulin. Russ J Org Chem 51, 715–726 (2015). https://doi.org/10.1134/S1070428015050231

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  • DOI: https://doi.org/10.1134/S1070428015050231

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