Synthesis of Heterocyclic Propellanes by 1, 3??Dipolar Cycloaddition of 2, 6??Dichlorobenzonitrile Oxide to 2, 3??Fused Indoles. Catalytic Hydrogenation of the …

…, E Coutouli??Argyropoulou

Index: Malamidou-Xenikaki, Elizabeth; Coutouli-Argyropoulou, Evdoxia Liebigs Annalen der Chemie, 1992 , # 1 p. 75 - 78

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Citation Number: 3

Abstract

Abstract N-Methylcycloalkano [b] indoles 1a, 1c–d and N-methylindeno [1, 2-b] indole (1e) react with 2, 6-dichlorobenzonitrile oxide (2) to afford regioselectively propellanes 3. Catalytic hydrogenation of compounds 3 proceeds via the labile β-hydroxyimines 4, which are further decomposed to the starting indole and 2, 6-dichlorobenzonitrile. In one case the intermediate imine 4e is stable and isolated in pure form.