Push‐pull‐Butadiene. XI. Darstellung und Reaktionen von Methylsulfonylnicotinonitrilen

Abstract

Push‐pull‐Butadienes. XI. Syntheses and Reactions of MethylsulfonylnicotinonitrilesMethylthionicotinonitriles 1, 3, 5, 9 and 12 react with potassium permanganate to give corresponding methylsulfonylnicotinonitriles 2, 4, 6, 10 and 13, respectively. Compounds 2 can be converted with sodium ethoxide to yield diethoxynicotinonitriles 7. Similarly 4, 5 and 6 react with sodium ethoxide to give 4‐aryl‐5‐bromo‐2,6‐diethoxy‐nicotinonitriles 8. Treatment of nicotinonitriles 9, 10 or 13 with sodium ethoxide gives diethoxynicotinonitriles 11. 2 with hydrazine hydrate together afford pyrazolo[3,4‐b]pyridines 14. However, an excess of hydrazine hydrate and 2 or 6 yields hydrazinopyrazolo[3,4‐b]pyridines 15.