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Issue 11, 2011
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Divergent reactions of indoles with aminobenzaldehydes: indole ring-opening vs. annulation and facile synthesis of neocryptolepine

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Abstract

Indoles display a diverse pattern of reactivity upon reaction with different classes of aminobenzaldehydes. Whereas the acid-promoted reaction with secondary aminobenzaldehyde leads to indole annulation followed by spontaneous oxidation to neocryptolepine and analogues, the reaction with primary aminobenzaldehydes results in the formation of synthetically useful quinolinesvia a remarkably facile indole ring-opening.

Graphical abstract: Divergent reactions of indoles with aminobenzaldehydes: indole ring-opening vs. annulation and facile synthesis of neocryptolepine

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Supplementary files

Article information


Submitted
25 Jul 2011
Accepted
04 Aug 2011
First published
19 Aug 2011

Chem. Sci., 2011,2, 2178-2181
Article type
Edge Article

Divergent reactions of indoles with aminobenzaldehydes: indole ring-opening vs. annulation and facile synthesis of neocryptolepine

M. K. Vecchione, A. X. Sun and D. Seidel, Chem. Sci., 2011, 2, 2178
DOI: 10.1039/C1SC00506E

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