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A general synthesis of substituted formylpyrroles from ketones and 4-formyloxazole.

Abstract
A novel two-step synthesis of substituted 2-formylpyrroles is described. Aldol adducts of ketones and 4-formyloxazole undergo a dehydration/oxazole hydrolysis/cyclization cascade on sequential treatment with MsCl/Et3N and aqueous NaOH to yield 5-substituted and 4,5-disubstituted 2-formylpyrroles. The methodology was extended to an N-benzyl thiazolium salt.
AuthorsJonathan T Reeves, Jinhua J Song, Zhulin Tan, Heewon Lee, Nathan K Yee, Chris H Senanayake
JournalOrganic letters (Org Lett) Vol. 9 Issue 10 Pg. 1875-8 (May 10 2007) ISSN: 1523-7060 [Print] United States
PMID17355146 (Publication Type: Journal Article)
Chemical References
  • 4-formyloxazole
  • Formates
  • Ketones
  • Oxazoles
  • Pyrroles
  • formic acid
Topics
  • Formates (chemistry)
  • Hydroxylation
  • Ketones (chemistry)
  • Molecular Structure
  • Oxazoles (chemistry)
  • Pyrroles (chemical synthesis, chemistry)

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