The retro Diels-Alder reaction as a valuable tool for the synthesis of heterocycles

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Abstract

Applications of the retro Diels-Alder reaction (cycloreversion) under mild conditions for the laboratory preparation of heteromonocycles or condensed-ring heterocycles are reviewed. A new method utilizes diendo- or diexo-3-aminonorbornene-2-carboxylic acids and their derivatives for the formation of heterocyclic ring systems which are difficult to access by other routes or which can be prepared only in complicated multi-step procedures. The synthesis of substituted 1,3-dienes (e.g. furan derivatives) and O,N- or N,N-heterocycles (oxazoles, isoxazoles, pyrazoles, imidazoles, triazoles, pyrimidinones, oxazinones, pyridazinones etc) are discussed.

Original languageEnglish
Pages (from-to)1423-1432
Number of pages10
JournalCurrent Organic Chemistry
Volume7
Issue number14
DOIs
Publication statusPublished - Sep 1 2003

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ASJC Scopus subject areas

  • Organic Chemistry

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