1-Dicyanomethylene-3-indanone (1) shows a remarkable reactivity of the carbonyl- and the methylene-function towards nucleophiles. With anilines and phenylhydrazine, resp., the deep-red colored pentamethinecyanines2and3are formed, azocoupling leads to indano-pyridazines4. With diphenylformamidines anilinomethylene-indanones5are obtained in a primary reaction, followed by ring closure and Dimroth-rearrangement to indano-pyridines6.13C- and15N-NMR-spectrocopy is used for confirmation of the structures.
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