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

✍ Scribed by Malamidou-Xenikaki, Elizabeth ;Coutouli-Argyropoulou, Evdoxia

Book ID
102368071
Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
379 KB
Volume
1992
Category
Article
ISSN
0947-3440

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✦ Synopsis

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.

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