Multi-component coupling reactions of aldehydes and amides with maleic anhydride: Synthesis of 7-oxo-6-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acids

Helfried Neumann, Axel Jacobi Von Wangelin, Dirk Gördes, Anke Spannenberg, Wolfgang Baumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

A new protocol for the synthesis of a series of 7-oxo-6-azabicyclo[3.2.1]oct-2-ene-8-carboxylic acids from simple aldehydes, amides and maleic anhydride was developed. Key step is an efficient three-component coupling reaction of two molecules of aldehyde with an amide to give a 1-acylamino-1,3-butadiene derivative which easily undergoes Diels-Alder addition to maleic anhydride. Thermic rearrangement of the cycloadducts affords the bicyclic target compounds. The new one-pot protocol gives higher yields than standard multi-step sequences due to the selective in situ trapping of one acylamino diene isomer. The target compounds can be further elaborated into arenes, cage molecules and natural product precursors.

Original languageEnglish
Pages (from-to)2381-2387
Number of pages7
JournalTetrahedron
Volume58
Issue number12
DOIs
StatePublished - 18 Mar 2002
Externally publishedYes

Keywords

  • 6-azabicyclo[3.2.1]octane
  • Aminodience
  • Bicyclic ketones
  • Bicylic lactams
  • Diels-Alder reaction
  • Maleic anhydride
  • Multi-component reaction

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