Carbon-Sulfur and Carbon-Selenium Double Bond Formation Through Thiolysis and Selenolysis of 4-Methylsulfanyl-Substituted Pyridinium and Quinolinium Halides

Jocelyne Levillain; Daniel Paquer; Aboubacary Sene; Michel Vazeux

doi:10.1055/s-1998-2002

Synthesis 1998; 1998(1): 99-104
DOI: 10.1055/s-1998-2002

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Carbon-Sulfur and Carbon-Selenium Double Bond Formation Through Thiolysis and Selenolysis of 4-Methylsulfanyl-Substituted Pyridinium and Quinolinium Halides

Jocelyne Levillain^* , Daniel Paquer, Aboubacary Sene, Michel Vazeux

^*Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507 ISMRA, Université de Caen, 6 Bd Maréchal Juin, F-14050 Caen Cedex, France

Abstract

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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.

Menshutkin and Zincke reactions - pyridinium and quinolinium salts - thiolysis - selenolysis - thioxo- and selenoxo-pyridine systems

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