Issue 2, 2000

Synthesis and stereochemistry of stereoisomeric 1,2,3-oxathiazino[4,3-a]isoquinolines

Abstract

The ring-closures of homocalycotomine and its 1′- and 2′-methyl-substituted diastereomers 3, 4 and 7, 8 with thionyl chloride or with sulfuryl chloride led to 1,2,3-oxathiazino[4,3-a]isoquinoline derivatives 9–11 and 18, 19 or to 15, 17 and 22, 23, respectively. The relative configurations and the predominant conformations of the cis1trans–cis2 conformational equilibrium were studied by means of 1H- and 13C-NMR spectroscopy, with the application of DNOE, 2D HSC and 2D-COSY measurements. In good agreement with the liquid-phase results, the X-ray investigations revealed that 9 and 10 have the cis1, while 18 has the trans-anellated stereostructure.

Supplementary files

Article information

Article type
Paper
Submitted
07 Sep 1999
Accepted
10 Nov 1999
First published
25 Jan 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 287-293

Synthesis and stereochemistry of stereoisomeric 1,2,3-oxathiazino[4,3-a]isoquinolines

P. Sohár, E. Forró, L. Lázár, G. Bernáth, R. Sillanpää and F. Fülöp, J. Chem. Soc., Perkin Trans. 2, 2000, 287 DOI: 10.1039/A907236E

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