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[5C + 1N] annulations: two novel routes to substituted dihydrofuro[3,2-c]pyridines.

Abstract
Two novel routes based on [5C + 1N] annulations for the synthesis of 2,3-dihydrofuro[3,2-c]pyridines are described. Ammonium acetate (NH(4)OAc) is used as an ammonia source in both routes. The first route utilizes 1-acyl-1-[(dimethylamino)alkenoyl]cyclopropanes as a five-carbon 1,5-bielectrophilic species and combines the [5C + 1N] annulation and regioselective ring-enlargement of cyclopropyl ketone into one pot, whereas the second route utilizes 3-acyl-2-[(dimethylamino)alkenyl]-4,5-dihydrofurans as the five-carbon synthons, which involves a sequential intermolecular aza-addition, intramolecular aza-nucleophilic addition/elimination, and dehydration reaction.
AuthorsPeng Huang, Rui Zhang, Yongjiu Liang, Dewen Dong
JournalOrganic letters (Org Lett) Vol. 14 Issue 20 Pg. 5196-9 (Oct 19 2012) ISSN: 1523-7052 [Electronic] United States
PMID23025242 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Pyridines
  • Carbon
  • Nitrogen
Topics
  • Carbon (chemistry)
  • Hydrogenation
  • Molecular Structure
  • Nitrogen (chemistry)
  • Pyridines (chemical synthesis)
  • Stereoisomerism

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