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Stepwise Synthesis of 2-Amino-3-Vinylindolizines Using a Mixture of N-Allyl-2-Halopyridinium Halides and CH Acid Derived from Acetonitrile

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Chemistry of Heterocyclic Compounds Aims and scope

N-Allyl-2-bromo- and N-allyl-2-chloropyridinium halides react with malonodinitrile and thiazolyl derivatives of acetonitrile in the presence of a twofold excess of triethylamine to provide nucleophilic substitution products, which undergo Thorpe cyclization smoothly upon treatment with KOH to give the corresponding 2-amino-3-vinylindolizines.

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Authors and Affiliations

  1. Luhansk T. Shevchenko National University, 2 Oboronnaya St., Luhansk, 91011, Ukraine

    N. M. Tverdokhleb & G. E. Khoroshilov

Authors
  1. N. M. Tverdokhleb
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  2. G. E. Khoroshilov
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Correspondence to G. E. Khoroshilov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1226-1231, August, 2013.

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Tverdokhleb, N.M., Khoroshilov, G.E. Stepwise Synthesis of 2-Amino-3-Vinylindolizines Using a Mixture of N-Allyl-2-Halopyridinium Halides and CH Acid Derived from Acetonitrile. Chem Heterocycl Comp 49, 1141–1145 (2013). https://doi.org/10.1007/s10593-013-1355-5

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  • DOI: https://doi.org/10.1007/s10593-013-1355-5

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