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Issue 19, 1996
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Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones

Abstract

The synthesis of trialkylpyrazines having methyl groups on C-2 and C-5 is described, which is completed by the cross-coupling reaction of 2-chloro-3,6-dimethylpyrazine with dialkylzinc in the presence of [1,3-bis(diphenylphosphino)propane] nickel(II) chloride. Similarly, 2,5-diisobutyl-, -diisopropyl- and -di-sec-butyl-3-methylpyrazines are prepared from the corresponding dialkyl chloropyrazines. The dimethyl products are acylated with an α-keto acid under the Minisci radical conditions providing 2-acyl-5-alkyl-3,6-dimethylpyrazines. Several compounds obtained in this study prove to be active as components of pheromones in ants.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1996, 2345-2350
Article type
Paper

Studies on pyrazines. Part 32. Synthesis of trisubstituted and tetrasubstituted pyrazines as ant pheromones

N. Sato and T. Matsuura, J. Chem. Soc., Perkin Trans. 1, 1996, 2345
DOI: 10.1039/P19960002345

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