3,4-Didehydropyridine plus cyclopentadiene: [2+2] or [4+2]-cycloaddition ?

Manfred G. Reinecke, E. Sherwood Brown, Bruce P. Capehart, David E. Minter, Richard K. Freeman

Research output: Contribution to journalArticle

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Abstract

3, 4-Didehydropyridine (2) generated from two precursors (6 and 7) of the diazonium carboxylate 5 reacts with cyclopentadiene to give the [ 4+2 ] -cyclo-addition product 3 rather than the [2+2]-adduct 4 proposed in the literature. The structure of 3 was supported by complete proton and carbon NMR assignments made with the aid of decoupling and 2D experiments.

Original languageEnglish (US)
Pages (from-to)5675-5680
Number of pages6
JournalTetrahedron
Volume44
Issue number18
DOIs
StatePublished - 1988

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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