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Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of N-arylcyanamides with (chloromethyl)thiirane in aqueous alkaline solution provides an easy synthetic approach to N-aryl-N-(thietan-3-yl)cyanamides. Yields vary from 34 to 76% and are lower in the case of electron-deficient aryl substituents. The reaction with phenols containing electron-withdrawing groups results in formation of 3-(aryloxy)thietanes in 19–45% yields.

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Authors and Affiliations

  1. University of Southern California, 837 Bloom Walk, Los Angeles, CA, 90089, USA

    A. N. Butkevich

  2. The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA

    M. Zibinsky

  3. Saint Petersburg State University, 26 Universitetskii Pr., St. Petersburg, 198504, Russia

    V. V. Sokolov & A. A. Tomashevskii

Authors
  1. A. N. Butkevich
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  2. M. Zibinsky
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  3. V. V. Sokolov
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  4. A. A. Tomashevskii
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Corresponding author

Correspondence to V. V. Sokolov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1809-1815, December, 2011.

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Butkevich, A.N., Zibinsky, M., Sokolov, V.V. et al. Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane. Chem Heterocycl Comp 47, 1509–1515 (2012). https://doi.org/10.1007/s10593-012-0941-2

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  • DOI: https://doi.org/10.1007/s10593-012-0941-2

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