ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of some thioxanthene derivatives as possible metabolites of Methixerc (VI-hydrochloride) is described. The VON BRAUN degradation of VI with cyanogen bromide leads to the demethyl derivative 9- [(3-piperidyl)-methyl]-thioxanthene (VIII). Oxidation of Methixen with hydrogen peroxide at 20° gives a mixture of the two steroisomerie sulfoxides IX and X; they were separated by preparative paper-chromatography. The same oxidant at 100° oxidizes Methixelz to the sulfone IV. This was also obtained by alkylation of thioxanthene-10, 10-dioxide (11). On oxidation with hydrogen peroxide the demethyl derivative VIII affords at 20° the sulfoxide XI (isolated in non-uniform steric state), and at 100° the sulfone V. Alkylation of thio-xanthene with N-methyl-3-chloromethyl-piperidine-N-oxide (I) leads to -[(N- methyl-3-piperidyl)-methyl]-thioxanthene-N-oxide (111), the constitution of which was proved by conversion to VI.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19630460402
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