Vilsmeier–Haack reactions of α-hydroxyketenedithioacetals: a facile synthesis of substituted pyridines
2002; Elsevier BV; Volume: 43; Issue: 12 Linguagem: Inglês
10.1016/s0040-4039(02)00174-0
ISSN1873-3581
AutoresAjith Dain Thomas, C. V. Asokan,
Tópico(s)Multicomponent Synthesis of Heterocycles
ResumoThe reaction of α-hydroxyketenedithioacetals, generated by the 1,2-addition of methyl Grignard reagent to α-oxoketenedithioacetals, with the Vilsmeier reagent was investigated. The reaction proceeds with acid-catalysed dehydration to afford sulphur substituted 1,3-butadienes, which undergo subsequent iminoalkylations. The intermediate iminium salts formed were successfully transformed into 2-methylsulfanyl substituted 4-aryl pyridines, in the presence of ammonium acetate
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