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Transformations of dibenzo(γ-oxopiperidino)aza-14-crowns-4 upon acylation. Molecular structure of dibenzo-16-crown-3

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Abstract

The result of acylation of dibenzoaza-14-crowns-4 containing a 4-oxopiperidine fragment with acetic anhydride depends on the substituent on the nitrogen atom. The NH-substrates initially undergo acylation at the piperidine nitrogen atom, followed by enolization and O-acylation. The acylation of N-methyl derivatives is accompanied by cleavage of the piperidine ring at the C-N bond with formation of acetylamino-substituted dibenzo-16-crowns-3. The structure of the latter was determined by X-ray analysis.

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Authors and Affiliations

  1. Russian University of Peoples’ Friendship, ul. Ordzhonikidze 3, Moscow, 117198, Russia

    A. N. Levov, An’ Le Tuan, A. T. Soldatenkov & Chyong Khong Khieu

  2. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow, Russia

    V. N. Khrustalev

Authors
  1. A. N. Levov
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  2. An’ Le Tuan
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  3. A. T. Soldatenkov
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  4. Chyong Khong Khieu
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  5. V. N. Khrustalev
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Corresponding author

Correspondence to A. T. Soldatenkov.

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Original Russian Text © A.N. Levov, Le Tuan An’, A.T. Soldatenkov, Chyong Khong Khieu, V.N. Khrustalev, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 617–620.

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Levov, A.N., Le Tuan, A., Soldatenkov, A.T. et al. Transformations of dibenzo(γ-oxopiperidino)aza-14-crowns-4 upon acylation. Molecular structure of dibenzo-16-crown-3. Russ J Org Chem 44, 612–616 (2008). https://doi.org/10.1134/S1070428008040246

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  • DOI: https://doi.org/10.1134/S1070428008040246

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