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Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc

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Abstract

2- and 4-(Arylmethylideneamino)phenols react with Reformatsky reagent, obtained from methyl 1-bromocyclohexanecarboxylate and zinc, to form 3-aryl-2-[2-(or 4-)hydroxyphenyl]-2-azaspiro[3.5]nonan-1-ones. The reaction involves the initial addition of the organozinc reagent across the C=N double bond of the Schiff base and the subsequent intramolecular cyclization of the adduct via the nucleophilic attack of the nitrogen atom on the ester carbonyl carbon atom. The structures of the products were confirmed by X-ray diffraction analysis.

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Funding

The work was financially supported by the Government of the Perm Krai.

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Authors and Affiliations

  1. Perm State National Research University, 614990, Perm, Russia

    E. A. Nikiforova, D. V. Baibarodskikh, D. P. Zverev, M. V. Dmitriev & N. F. Kirillov

Authors
  1. E. A. Nikiforova
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  2. D. V. Baibarodskikh
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  3. D. P. Zverev
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  4. M. V. Dmitriev
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  5. N. F. Kirillov
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Correspondence to E. A. Nikiforova.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 8, pp. 1154–1160 https://doi.org/10.31857/S0514749221080061.

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Nikiforova, E.A., Baibarodskikh, D.V., Zverev, D.P. et al. Reaction of 2- and 4-(Arylmethylideneamino)phenols with Methyl 1-Bromocyclohexanecarboxylate and Zinc. Russ J Org Chem 57, 1275–1280 (2021). https://doi.org/10.1134/S1070428021080066

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  • DOI: https://doi.org/10.1134/S1070428021080066

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