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Trapping of photochemical intermediates as a tool in organic synthesis. Preparation of spiroaziridinopyridones, a new heterocyclic system

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
43
Issue
52
Identifiers
DOI: 10.1016/s0040-4039(02)02438-3
Keywords
  • Condensed Pyridines
  • Photochemical Intermediates Trapping
  • Ketenimines
  • Aziridines

Abstract

Abstract Whereas alkyl lithium and Grignard reagents both at rt and at −80°C thermally react with 3-methylisoxazolo[5,4- b]pyridine giving alkylation and/or isoxazole ring opening products, sodium malonate and sodium boron hydride react only under UV irradiation. Selective trappings of ketenimine or azirine intermediates give an enaminopyridone or two diasteroisomeric spiroaziridinopirydones. Regioselective opening of the aziridine ring with perchloric acid gives 3(1-amino-ethyl)-1 H-pyridin-2-one.

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