Synthetic Communications p. 159 - 168 (2017)
Update date:2022-07-30
Topics: Characterization Reagents Mechanism Workup and Isolation Reaction Conditions
Mal’kina, Anastasiya G.
Nosyreva, Valentina V.
Albanov, Alexander I.
Afonin, Andrei V.
Vashchenko, Alexander V.
Amosova, Svetlana V.
Trofimov, Boris A.
Regioselective N(2)-H-cyanoethylation of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile proceeds under mild conditions (14% KOH, acetone/H2O, 35 °C, 6–21 h) to afford 1-(2-сyanoethyl)-2-[(E)-aryl(heteroaryl)methylidene]-1-hydrazinecarbothioamides in up to 74% yields. The synthesized thioamides are promising precursors of novel families of functionalized thiosemicarbazones as exemplified by hydrolysis of their cyano group to the corresponding amido function (46.5–60% yields).
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