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Synthesis and Some Transformations of New Acetophenone Derivatives Containing a Carbamate Moiety

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Abstract

The acylation of methyl phenylcarbamate, 2-(morpholin-4-yl)ethyl phenylcarbamate, and 2-(pyri­din-2-yl)ethyl phenylcarbamate with acetic anhydride in polyphosphoric acid at 50–55°C (3 h) involved the para position with respect to the carbamate group with the formation of the corresponding acetophenones. Methyl 2-methoxyphenylcarbamate was acylated under similar conditions to give methyl 5-acetyl-2-methoxy­phenylcarbamate. Methyl 4- and 2-acetylphenylcarbamates reacted with N-bromosuccinimide in the presence of copper(II) acetate and DMF at 80°C and with HCl and HBr in the presence of DMSO in ethyl acetate at 30–33°C to afford methyl [4(2)-(2-dimethylamino-2-oxoacetyl)phenyl]carbamates and methyl [4(2)-(2-bromo-2-chloroacetyl)phenyl]carbamates, respectively. The condensation of 2-(morpholin-4-yl)ethyl and 2-(pyridin-2-yl)­ethyl (4-acetylphenyl)carbamates with 4-methoxybenzaldehyde in methanolic potassium hydroxide furnished the corresponding chalcones.

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Authors and Affiliations

  1. Astrakhan State University, 414000, Astrakhan, Russia

    A. V. Velikorodov, E. N. Kutlalieva & S. B. Nosachev

  2. Astrakhan State Medical University, Ministry of Health of the Russian Federation, 414000, Astrakhan, Russia

    A. V. Velikorodov, E. N. Kutlalieva & E. A. Shustova

Authors
  1. A. V. Velikorodov
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  2. E. N. Kutlalieva
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  3. S. B. Nosachev
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  4. E. A. Shustova
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Correspondence to A. V. Velikorodov.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 1, pp. 97–105 https://doi.org/10.31857/S0514749223010081.

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Velikorodov, A.V., Kutlalieva, E.N., Nosachev, S.B. et al. Synthesis and Some Transformations of New Acetophenone Derivatives Containing a Carbamate Moiety. Russ J Org Chem 59, 60–66 (2023). https://doi.org/10.1134/S1070428023010062

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