A Synthetic Application of Methylthioacetonitrile. I. A Synthesis of cis- and trans-β-Arylacrylonitriles, β, γ-Unsaturated Nitriles and Carbonyl Compounds

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The Knoevenagel condensation of methylthioacetonitrile with carbonyl compounds such as benzaldehyde, cyclopentanone, phenylacetone, was examined to give the corresponding α-methylthio unsaturated nitriles. Desulfurization of β-aryl-α-methylthioacrylonitriles (5a-f) with Raney Nickel afforded cis-β-arylacrylonitriles (6a-f). Reduction of 5a-c with sodium borohydride gave α-methylthiophenylpropionitriles (7a-c), which were converted to trans-cinnamonitriles (9a-c). α-Methylthio-α, β-unsaturated nitriles (11a-d) were lead to α-ethyl-α-methylthio-β, γ-unsaturated nitriles (12a-d). Furthermore, the α-methylthiophenylpropionitrile (7b) was converted to 4-methoxybenzyl methyl ketone.
社団法人日本薬学会の論文
1978-06-25