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Transformations of N-(2-acylaryl)benzamides and their analogs under the Camps cyclization conditions

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Abstract

N-(2-Acylaryl)benzamides and analogous N-substituted furan-2-, thiophene-2-, and cyclopropane-carboxamides in the systems EtONa–EtOH, EtONa–THF, and t-BuOK–t-BuOH undergo Camps cyclization to 2-aryl-, 2-hetaryl-, and 2-cyclopropylquinolin-4(1H)-ones with high yields. The same substrates in the system t-BuOK (5 equiv)–THF are converted mainly to the corresponding N-(2-hydroxyaryl) amides as a result of oxidative transformation of the acyl fragment into hydroxy group.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119991, Russia

    S. S. Mochalov, A. N. Fedotov, E. V. Trofimova & N. S. Zefirov

Authors
  1. S. S. Mochalov
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  2. A. N. Fedotov
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  3. E. V. Trofimova
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  4. N. S. Zefirov
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Corresponding author

Correspondence to A. N. Fedotov.

Additional information

Original Russian Text © S.S. Mochalov, A.N. Fedotov, E.V. Trofimova, N.S. Zefirov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 7, pp. 964–976.

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Mochalov, S.S., Fedotov, A.N., Trofimova, E.V. et al. Transformations of N-(2-acylaryl)benzamides and their analogs under the Camps cyclization conditions. Russ J Org Chem 52, 956–969 (2016). https://doi.org/10.1134/S107042801607006X

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  • DOI: https://doi.org/10.1134/S107042801607006X

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