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Hydrazine-assisted one-pot depropargylation and reduction of functionalized nitro calix[4]arenes

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Abstract

Calix[4]arene derivatives containing two or four O-propargyl moieties are capable of undergoing reductive depropargylation in the presence of hydrazine hydrate. The propargyl groups are removed in the form of 4,5-dihydro-1H-pyrazoles, which allowed proposing a reasonable mechanism for the depropargylation. The propargyl group can be used as the protection for the selective nitration at the distal positions of the upper rim of di-O-propargyl-substituted calix[4]arene and p-tert-butylcalix[4]arene. The reduction of nitro group at the upper rim proceeds along with the depropargylation upon the addition of a nickel catalyst to the reaction mixture with hydrazine hydrate, which leads to calixarenamines containing free hydroxy groups.

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Authors and Affiliations

  1. Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    V. A. Burilov, R. N. Belov & I. S. Antipin

  2. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS, 8 ul. Acad. Arbuzova, 420088, Kazan, Russian Federation

    S. E. Solovieva

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  1. V. A. Burilov
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  2. R. N. Belov
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  3. S. E. Solovieva
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  4. I. S. Antipin
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Corresponding author

Correspondence to V. A. Burilov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

This work was financially supported by the Russian Science Foundation (Project No. 22-13-00304).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 4, pp. 948––954, April, 2023.

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Burilov, V.A., Belov, R.N., Solovieva, S.E. et al. Hydrazine-assisted one-pot depropargylation and reduction of functionalized nitro calix[4]arenes. Russ Chem Bull 72, 948–954 (2023). https://doi.org/10.1007/s11172-023-3858-4

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  • DOI: https://doi.org/10.1007/s11172-023-3858-4

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