The synthesis and stereochemistry of derivatives of 1,2,3,4,6,11,12,13,14,14a-decahydropyrido[1,2-b][2]benzazonine. Crystal structure of 1,2,3,4,4a,5,6,7,7a,12-decahydro-7-phenylisoindolo[1,2-d]quinolizin-13-ium tosylate
- 1 January 1989
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 2431-2435
- https://doi.org/10.1039/p19890002431
Abstract
Catalytic reduction of the pyridine ring of 2-phenyl-2-[2-(2-pyridyl)ethyl]indan-1,3-dione gives, by ring opening of the initially produced carbinolamine, 12-phenyl-1,2,3,4,12,13,14,14a-octahydropyrido[1,2-b]benzazonine-6,1 1-dione. This adopts a piperidine ring conformation with an axial alkyl residue, and the low-temperature 13C n.m.r. spectrum shows the presence of two rotamers about the N-aroyl moiety. The derived 11-hydroxy-1 2-phenyldecahydropyrido[1,2-b][2]benzazonine prefers the trans-fused ring conformation and attempts to form the toluene-p-sulphonate of this gave rel-(4aR,7R,7aR,13R)-1,2,3,4,4a,5,6,7,7a,12-decahydro-7-phenylisoindolo[1,2-d]quinolizin-13-ium tosylate. An X-ray structural analysis of the tosylate was performed.Keywords
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