Abstract
4-Methylsulfanylpyridinium and -quinolinium salts 3 and 4 with alkyl groups such as methyl, allyl, benzyl, ethoxycarbonylmethyl, benzoylmethyl on the nitrogen atom were prepared by the Menschutkin-type reaction and some of them caused to react under either the thiolysis or selenolysis reaction conditions. N-Substituted pyridine-4-thiones 5 a - c and quinoline-4-thiones 6 a - e were formed at different rates in high isolated yield. On the other hand, two N-alkyl-4-selenopyridones 7 a,b together with three 4-selenoquinolones, 8 a,b,c were also produced in high chemical purity and characterized spectroscopically. In addition, 4, sulfanylpyridone 12 and 4-selenopyridone 13 with a N-tert-butyl group were obtained via Zincke's salt 9. The overall process provides a useful alternative to the otherwise difficult direct N-alkylation of thioxo- and selenoxopyridine systems.
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