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Synthesis 1992; 1992(8): 798-802
DOI: 10.1055/s-1992-26229
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Synthesis of New Heterotricyclic Compounds Containing the [1,8]Naphthyridine Group by Thermal Isomerization of 2-Dialkylamino-3-vinylpyridines

Vicente Ojea* , Carlos Peinador, José M. Quintela
  • *Departamento de Química Fundamental e Industrial, Facultad de Ciencias, Universidad de La Coruña, E-15071 La Coruña, Spain
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Publication Date:
17 September 2002 (online)

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2-N,N-Dialkylamino-3-(2,2-dicyanovinyl)pyridines react thermally in polar solvents via [1,5] hydrogen transfer followed by carbon-carbon bond formation to yield heterotricyclic compounds containing the [1,8]naphthyridine group. The reaction time is markedly dependent on the solvent used and the stereoelectronic effects of the amino moiety. The presence of thiazolidinyl group results in the thermal isomerization taking place regiospecifically.

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