Abstract
Push‐pull‐Butadienes. VI. Synthesis of Substituted Nicotinonitriles2‐Aryl‐4,4‐bis(methylthio)‐1,3‐butadiene‐1,1‐dicarbonitriles 1 react with N‐bromosuccinimide or sulphuryl chloride to give 3‐bromo‐ and 3‐chloro‐butadienedicarbonitriles 3, respectively. Compounds 1 or 3 can be converted with methanethiol in alkaline solution to 4‐aryl‐2,6‐bis(methylthio)nicotinonitriles 2. Butadienedicarbonitriles 3 and sodium alkoxide yield alkoxynicotinonitriles 5. 4‐Aryl‐2,6‐dibromo‐ and 2‐bromo‐5‐chloro‐nicotinonitriles 8, respectively, are prepared by treating 1 or 3 with bromine. Nicotinonitriles 8 react with hydrazine hydrate to yield pyrazolo[3,4‐b]pyridines 12. Treatment of butadienedicarbonitriles 3 with sulphuryl chloride gives 2‐aryl‐3‐bromo‐ and 3‐chloro‐4‐chloromethylthio‐4‐methylthio‐1,3‐butadiene‐1,1‐dicarbonitriles 17, respectively. The structures of the prepared compounds are in agreement with spectroscopic data.
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