Synthesis of Heterocyclic Propellanes by 1,3‐Dipolar Cycloaddition of 2,6‐Dichlorobenzonitrile Oxide to 2,3‐Fused Indoles. Catalytic Hydrogenation of the Cycloadducts
Authors:
- 13 January 1992
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1992 (1) , 75-78
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.Keywords
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