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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 47, 2017 - Issue 2
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Original Articles

Regioselective N(2)-H-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile

Anastasiya G. Mal’kinaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian Federation
,
Valentina V. NosyrevaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian Federation
,
Alexander I. AlbanovA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian Federation
,
Andrei V. AfoninA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian Federation
,
Alexander V. VashchenkoA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian Federation
,
Svetlana V. AmosovaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian Federation
&
Boris A. TrofimovA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, Russian FederationCorrespondence[email protected]
 show all
Pages 159-168 | Received 14 Sep 2016, Published online: 11 Nov 2016
 
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ABSTRACT

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).

GRAPHICAL ABSTRACT

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Related Research Data

Regioselective N(2)-H-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile
Source: Figshare
CCDC 1498046: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
CCDC 1498047: Experimental Crystal Structure Determination
Source: Cambridge Crystallographic Data Centre
Regioselective N(2)-H-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile
Source: Figshare
Regioselective N(2)-H-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes with acrylonitrile
Source: Taylor & Francis

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