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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 22
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Original Articles

Unexpected ipso-Substitutions at the β-Carboline Nucleus

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Pages 3843-3850 | Received 10 May 2003, Published online: 19 Aug 2006
 

Abstract

Minisci-type radical carbamoylation of 1-bromo-β-carboline (1) gives the 3-substituted product in low yield, whereas 1-acetyl-β-carboline (3a) reacts under ipso-substitution of the acetyl group. Cyanations of the N-oxides of 1 and 3a occur under clean ipso-substitution of the groups in 1-position. 1-Methyl derivatives show no tendency to react under ipso-substitution.

Acknowledgment

We thank the Fonds der Chemischen Industrie for financial support.

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