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Synthesis and X-ray Structural Studies of a Substituted 2,3,4,5-Tetrahydro-1H-3-benzazonine and a 1,2,3,5-Tetrahydro-4,3-benzoxazonine

Journal Article


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Abstract


  • Using a common 1-(1-phenylethenyl)-1,2,3,4-tetrahydroisoquinoline precursor to the required ylide or N-oxide intermediate, the Stevens [2,3] and analogous Meisenheimer [2,3] sigmatropic rearrangements have been applied to afford concise syntheses of phenyl -substituted representatives of each of the reduced 1H-3-benzazonine and 4,3-benzoxazonine systems, respectively. Single crystal X-ray structure determinations were employed to define the conformational characteristics for each ring type.

UOW Authors


  •   Bailey, Timothy S. (external author)
  •   Bremner, John
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2015

Citation


  • Bailey, T. S., Bremner, J. B., Skelton, B. W. & White, A. H. (2015). Synthesis and X-ray Structural Studies of a Substituted 2,3,4,5-Tetrahydro-1H-3-benzazonine and a 1,2,3,5-Tetrahydro-4,3-benzoxazonine. Molecules, 20 (1), 487-502.

Scopus Eid


  • 2-s2.0-84921447346

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3440&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2421

Number Of Pages


  • 15

Start Page


  • 487

End Page


  • 502

Volume


  • 20

Issue


  • 1

Abstract


  • Using a common 1-(1-phenylethenyl)-1,2,3,4-tetrahydroisoquinoline precursor to the required ylide or N-oxide intermediate, the Stevens [2,3] and analogous Meisenheimer [2,3] sigmatropic rearrangements have been applied to afford concise syntheses of phenyl -substituted representatives of each of the reduced 1H-3-benzazonine and 4,3-benzoxazonine systems, respectively. Single crystal X-ray structure determinations were employed to define the conformational characteristics for each ring type.

UOW Authors


  •   Bailey, Timothy S. (external author)
  •   Bremner, John
  •   Skelton, Brian W. (external author)
  •   White, Allan H. (external author)

Publication Date


  • 2015

Citation


  • Bailey, T. S., Bremner, J. B., Skelton, B. W. & White, A. H. (2015). Synthesis and X-ray Structural Studies of a Substituted 2,3,4,5-Tetrahydro-1H-3-benzazonine and a 1,2,3,5-Tetrahydro-4,3-benzoxazonine. Molecules, 20 (1), 487-502.

Scopus Eid


  • 2-s2.0-84921447346

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=3440&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/2421

Number Of Pages


  • 15

Start Page


  • 487

End Page


  • 502

Volume


  • 20

Issue


  • 1