Application of furan as a diene: Preparation of condensed 1,3-oxazines by retro-Diels-Alder reactions

Géza Stájer, Ferenc Miklós, Iván Kanizsai, Ferenc Csende, Reijo Sillanpää, Pál Sohár

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

(Di-exo-3-amino-7-oxabicyclo[2.2.1]hept-5-en-2-yl)methanol (3) was treated with oxo carboxylic acids [p-toluoylpropionic acid, cis- or trans-(p-toluoyl) cyclohexanecarboxylic acid, -benzoic acid or methanobenzocyclooctenecarboxylic acid] to furnish the oxanorbornene-fused pyrrolo[1,3]oxazine 4, the isoindolo[1,3]oxazines 5 and 6, and the methanobenzocyclooctenepyrrolo[1,3] oxazine 10, together with the retro-Diels-Alder products pyrrolooxazinone 7, oxazinoisoindolones 8 and 9, and oxazinopyrrolobenzocyclooctene 11. On reflux in chlorobenzene, furan was released from the oxanorbornene heterocycles 5 and 10 to give the retro-Diels-Alder products. The structures of the new compounds were established by NMR spectroscopy and also (for 6 and 9) by single-crystal X-ray structure determination.

Original languageEnglish
Pages (from-to)3701-3706
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Aug 27 2004

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Keywords

  • 1,3-Oxazines
  • NMR
  • Oxanorbornenes
  • Pyrrole-fused heterocycles
  • Retro-Diels-Alder reaction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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