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Synthese einiger Thioxanthen‐Derivate
Author(s) -
Schindler O.,
Lehner H.,
Michaelis W.,
Schmutz J.
Publication year - 1963
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19630460402
Subject(s) - chemistry , sulfone , hydrogen peroxide , sulfoxide , alkylation , medicinal chemistry , derivative (finance) , cyanogen bromide , piperidine , xanthene , organic chemistry , catalysis , biochemistry , peptide sequence , financial economics , economics , gene
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.