Synthesis of Highly Substituted Pyridines via [4 + 2] Cycloadditions of Vinylallenes and Sulfonyl Cyanides
2019; American Chemical Society; Volume: 85; Issue: 2 Linguagem: Inglês
10.1021/acs.joc.9b02628
ISSN1520-6904
AutoresSamuel G. Bartko, Phillip J. Hamzik, Leandro Espíndola, Christian Gomez, Rick Danheiser,
Tópico(s)Chemical synthesis and alkaloids
ResumoA convergent strategy for the synthesis of multisubstituted pyridines is described. Vinylallenes combine with commercially available arylsulfonyl cyanides in Diels-Alder cycloadditions to generate isopyridine cycloadducts that are converted to pyridines upon further heating or addition of a base. The 2-sulfonylpyridine products undergo nucleophilic aromatic substitution reactions with oxygen and carbon nucleophiles to provide access to a variety of highly substituted pyridines.
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