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Synthesis of Adamantylated Salicylic Acids

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Abstract

5-[3(4)-R-Adamantan-1-yl]salicylic acids [R = H, Alk, Ar, OH, NHC(S)NH2] have been synthesized by electrophilic substitution reactions of hydroxy- and bromoadamantanes with salicylic acid, as well as by reactions of 5-(3-hydroxyadamantan-1-yl)salicylic acid with carbon and nitrogen nucleophiles, in trifluoroacetic acid. The possibility of selective hydroxylation of the adamantane fragment in 5-(adamantan-1-yl)salicylic acid with sulfuric acid in trifluoroacetic anhydride has been demonstrated.

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Funding

This study was performed in the framework of the state program “Petrochemistry and Catalysis. Rational Use of Carbon-Containing Raw Materials” (project no. 121031300092-6).

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, 119992, Moscow, Russia

    E. A. Shokova & V. V. Kovalev

Authors
  1. E. A. Shokova
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  2. V. V. Kovalev
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Correspondence to V. V. Kovalev.

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The authors declare no conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 7, pp. 994–1005 https://doi.org/10.31857/S0514749221070090.

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Shokova, E.A., Kovalev, V.V. Synthesis of Adamantylated Salicylic Acids. Russ J Org Chem 57, 1089–1097 (2021). https://doi.org/10.1134/S1070428021070095

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