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1,2,4-Triazine in Organic Synthesis. 16. Reactivity of 3-Substituted 6-Phenyl-1,2,4-triazines towards Phenylacetonitrile Anion in Polar Aprotic Solvents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reactions of 3-X-6-phenyl-1,2,4-triazines (X = SMe, SPh, SO2Ph) with phenylacetonitrile anion in DMF were studied. In these reactions the ring transformation product 3-amino-4,6-diphenylpyridazine, the covalent addition product 3-X-5-(α-cyanobenzyl)-6-phenyl-2,5-dihydro-1,2,4-triazine, and the ipso-substitution product 3-(1-cyano-1-phenylmethyl)-6-phenyl-1,2,4-triazine were obtained. Analogous reactions carried out in DMA gave only the addition products in excellent yields as diastereomeric mixtures of the corresponding 2,5-dihydro-1,2,4-triazines.

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Authors and Affiliations

  1. Institute of Chemistry, University of Podlasie, ul. 3-go Maja 54, 08-110, Siedlce, Poland

    A. Rykowski & E. Wolinska

  2. Laboratory of Organic Chemistry, University of Wageningen, Dreijenplein 8, 6703 HB, Wageningen, The Netherlands

    H. C. van der Plas

Authors
  1. A. Rykowski
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  2. E. Wolinska
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  3. H. C. van der Plas
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Rykowski, A., Wolinska, E. & van der Plas, H.C. 1,2,4-Triazine in Organic Synthesis. 16. Reactivity of 3-Substituted 6-Phenyl-1,2,4-triazines towards Phenylacetonitrile Anion in Polar Aprotic Solvents. Chemistry of Heterocyclic Compounds 37, 1418–1423 (2001). https://doi.org/10.1023/A:1017959403370

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  • DOI: https://doi.org/10.1023/A:1017959403370

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