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Synthesis 2019; 51(12): 2548-2552
DOI: 10.1055/s-0037-1611532
paper
© Georg Thieme Verlag Stuttgart · New York

Formation of Aryl [1-Cyano-4-(dialkylamino)butadienyl] Ketones from Pyridines

Hyo Jin Gim
,
Michael E. Jung  *
Department of Chemistry and Biochemistry, University of California Los Angeles, Los Angeles, CA 90095, USA   eMail: jung@chem.ucla.edu
› InstitutsangabenWe thank the California Institute for Regenerative Medicine (CIRM) program at UCLA for support.
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Publikationsverlauf

Received: 07. März 2019

Accepted after revision: 10. April 2019

Publikationsdatum:
02. Mai 2019 (online)

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Abstract

Treatment of 2-chloropyridine with LDA and the Weinreb amide of benzoic acid afforded three unusual products, namely N-methylbenzamide, 2-chloropyridine-3-methanol, and the ring-opened addition product. This same final product could also be obtained from 2-chloro-3-benzoylpyridine on treatment with LDA. Mechanistic insight for the formation of these products is provided.

Key words

pyridines - Weinreb amides - LDA - pyridine ring-openings - anions

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611532.
  • Supporting Information
 

  • References

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