Synthesis of 3-azabicyclo[3.3.1]Nonane-6,9-diones

Brian D. Williams, Birute Williams, Francis Bernardoni, Robert C. Finn, Jon Zubieta

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A one pot synthesis of 3-azabicyclo[3.3.1]nonane-6,9-diones is described via the additibn of acryloyl chloride to enamines of N-carboxy-4 piperidones. Yields of bicycle were highest when additions were made to vigorously boiling solutions of morpholine enamines. X-Ray analysis of an azabicyclic system revealed a chair-chair structure to be the preferred conformation. Hydrolysis of 3-azabicyclo[3.3.1]nonane-6,9-diones (IIa) and (IIb) yielded the monocyclic carboxylic acids (IIIa) and (IIIb).

Original languageEnglish (US)
Pages (from-to)2199-2206
Number of pages8
JournalHeterocycles
Volume55
Issue number11
DOIs
StatePublished - Nov 1 2001

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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