Synthèse de dérivés de la 4-(méthylnitroasamino)-1-(3-pyridyl)-1-butanone (NNK)

Abstract : AIn this work we report the synthesis of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone derivatives (abbreviated NNK), which was divided in two parts. The first one was about the synthesis of NNK derivatives linked with an omega-functionalized aliphatic chain on the nitrosamine function. The key intermediate in this synthesis was the 3-[2-(3-pyridinyl)-1,3-dioxolan-2-yl]propylamine. The primary aliphatic amine was monoalkylated to introduce various omega-functionalized chains. The second one used functionalization of the pyridine ring. We studied 2 ways, one using 2,5-disubstituted mono or dihalogenated pyridines which didn't afford the expected 1-(6-chloro-3-pyridinyl)-4-(1-methyl-2-oxohydrazino)-1-butanone. The other way using ethyl 6-chloronicotinate derivatives was a good alternative to synthesize the target molecule. The chlorine atom present on the molecule may be used to introduce an aliphatic omega-functionalized chain
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Thomas Kaminski. Synthèse de dérivés de la 4-(méthylnitroasamino)-1-(3-pyridyl)-1-butanone (NNK). Autre. Université Paul Verlaine - Metz, 2007. Français. ⟨NNT : 2007METZ046S⟩. ⟨tel-01752689⟩

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