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Reactions of 2,3-Dibromo-2-methylpropanamides Promoted by Potassium tert-Butoxide

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Abstract

2,3-Dibromo-2-methylpropanamides with different substituents on the nitrogen atom were synthe­sized, and their transformations by the action of potassium tert-butoxide in THF were studied. 2,3-Dibromo-N-(4-methoxyphenyl)-2-methylpropanamide and 2,3-dibromo-N-(2,5-dibromo-4-methoxyphenyl)-2-methyl­propan­amide reacted with 1–2 equiv of t-BuOK to give the corresponding N-substituted 3-bromo-3-methyl- and 3-methylideneazetidin-2-ones with acceptable yields and selectivity. Increase of the amount of t-BuOK to 3–5 equiv led to significant reduction of the yield of vinyl bromides and 3-methylideneazetidin-2-ones. On the other hand, the reaction of 2,3-dibromo-N-(tert-butyl)-2-methylpropanamide with t-BuOK afforded 3-(tert-bu­toxymethyl)-1-tert-butylazetidin-2-one with a good yield and selectivity.

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ACKNOWLEDGMENTS

The spectral and analytical data were obtained using the equipment of the Chemistry joint center (Ufa Institute of Chemistry, Russian Academy of Sciences).

Funding

This study was performed in the framework of state assignment no. AAAA-A20-120012090021-4.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    A. M. Galeeva, Z. R. Valiullina, N. K. Selezneva & M. S. Miftakhov

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  1. A. M. Galeeva
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  2. Z. R. Valiullina
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  3. N. K. Selezneva
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  4. M. S. Miftakhov
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Corresponding author

Correspondence to Z. R. Valiullina.

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The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 10, pp. 1457–1465 https://doi.org/10.31857/S0514749221100128.

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Galeeva, A.M., Valiullina, Z.R., Selezneva, N.K. et al. Reactions of 2,3-Dibromo-2-methylpropanamides Promoted by Potassium tert-Butoxide. Russ J Org Chem 57, 1643–1649 (2021). https://doi.org/10.1134/S1070428021100122

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