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A solution-phase parallel synthesis of alkylated guanidines from thioisocyanates and amines

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Abstract

An efficient solution-phase parallel synthesis of alkylated guanidines from commercial thioisocyanates and amines is described. In the first step, a thioisocyanate reacts with one equivalent of ammonia or a primary or secondary amine to give a thiourea intermediate. The latter is S-alkylated with n-dodecyl bromide resulting in the corresponding thiouronium bromide. Finally, the reaction of the thiouronium salt with a second equivalent of ammonia or a primary amine yields an alkylated guanidine. All three synthetic steps are easily combined in a one-pot high-yielding procedure with a simple work-up. Ca. 250 guanidine derivatives with high structural and functional diversity were synthesized by the developed method. 35 representatives reported in this study were fully characterized.

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Authors and Affiliations

  1. Enamine Ltd., 23 Alexandra Matrosova Street, Kiev, 01103, Ukraine

    Andrey V. Bogolubsky, Alexander Grishchenko, Alexander Chuprina & Andrey Tolmachev

  2. The Institute of High Technologies, Kiev National Taras Shevchenko University, 4 Glushkov st., Building 5, Kiev,  03187, Ukraine

    Anzhelika Konovets

  3. ChemBioCenter, Kiev National Taras Shevchenko University, Chervonotkatska Street 61, Kiev,  02094 , Ukraine

    Sergey E. Pipko, Andrey Tolmachev, Alexander N. Boyko, Alexey Chekotylo & Oleg Lukin

Authors
  1. Andrey V. Bogolubsky
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  2. Alexander Grishchenko
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  3. Sergey E. Pipko
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  4. Anzhelika Konovets
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  5. Alexander Chuprina
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  6. Andrey Tolmachev
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  7. Alexander N. Boyko
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  9. Oleg Lukin
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Correspondence to Oleg Lukin.

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Bogolubsky, A.V., Grishchenko, A., Pipko, S.E. et al. A solution-phase parallel synthesis of alkylated guanidines from thioisocyanates and amines. Mol Divers 17, 471–477 (2013). https://doi.org/10.1007/s11030-013-9444-z

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  • DOI: https://doi.org/10.1007/s11030-013-9444-z

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