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Molecules 2015, 20(1), 487-502; doi:10.3390/molecules20010487

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

1
Department of Chemistry, University of Tasmania, Hobart, Tas. 7001, Australia
2
Tasmanian Alkaloids Pty Ltd, P.O. Box 130, Westbury, Tas. 7303, Australia
3
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia
4
School of Chemistry and Biochemistry M310, The University of Western Australia, Crawley, WA 6009, Australia
5
Centre for Microscopy, Characterisation and Analysis, M010, The University of Western Australia, Crawley, WA 6009, Australia
*
Author to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Received: 9 November 2014 / Accepted: 29 December 2014 / Published: 31 December 2014
View Full-Text   |   Download PDF [2676 KB, uploaded 31 December 2014]   |  

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. View Full-Text
Keywords: large rings; X-ray crystal structures; benzazonine; benzoxazonine large rings; X-ray crystal structures; benzazonine; benzoxazonine
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Bailey, T.S.; Bremner, J.B.; Skelton, B.W.; White, A.H. 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 2015, 20, 487-502.

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