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Synthesis of 6-substituted tetrahydropyridinones and cyclization to indolizidine and quinolizidine structures

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
25
Identifiers
DOI: 10.1016/s0040-4039(03)01096-7
Keywords
  • Thio-Substituted 3-Sulfolenes
  • Aza-Diels–Alder Reactions
  • Hg(Ii) Ions
  • Quinolizidines
  • Indolizidines

Abstract

Abstract 3-Sulfolenes 1 with various substituents at C-2 underwent [4+2] cycloaddition reactions with p-toluenesulfonyl isocyanate to give the teterahydropyridinones 4 . Through N-detosylation and Hg(II)-mediated electrophilic addition/intramolecular cyclization of 4e and 4f , the indolizidine and quinolizidine compounds 7a / 7b and 8 were synthesized, respectively.

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