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Dual reactivity of 1,2-disubstituted dihydro-N-heteroaromatic systems

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The effect of the nature of the electrophile and the heteroring on the direction of reactions involving the aromatization of α-substituted N-acyl dihydro-N-heterocycles with perchlorates of various organic cations was studied. It is shown that hard and intermediate electrophilic agents (triphenylmethyl, triindolylmethyl, and acetylium perchlorates) split out the α substituent from the dihydroheterocycles to give stable N-acyl salts of the corresponding bases. Soft acceptors (2,2,6,6-tetramethyl-1-oxopiperidinium perchlorate) split out a hydride ion in all cases to give α-substituted N-acyl salts of the corresponding bases.

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Authors and Affiliations

  1. Donetsk State University, 340055, Donetsk

    T. V. Stupnikova, Z. M. Skorobogatova & A. K. Sheinkman

Authors
  1. T. V. Stupnikova
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  2. Z. M. Skorobogatova
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  3. A. K. Sheinkman
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 946–950, July, 1979.

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Stupnikova, T.V., Skorobogatova, Z.M. & Sheinkman, A.K. Dual reactivity of 1,2-disubstituted dihydro-N-heteroaromatic systems. Chem Heterocycl Compd 15, 773–777 (1979). https://doi.org/10.1007/BF00473561

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  • DOI: https://doi.org/10.1007/BF00473561

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