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Issue 9, 2015
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Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization–oxidative Heck cascade and characterization as sirtuin modulators

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Abstract

An extension of our reported protocol to benzofused heterocyclic derivatives (benzofurans, indoles, isochromeneimines), involving a palladium-induced cascade of N-cyclization and oxidative Heck reactions of o-alkynylanilines, has allowed the preparation of indolobenzazepinones (paullones) with an alkylidene group at C7 in just 3–4 steps from ortho-iodoanilines. Some of these compounds behave as Sirt1 activators in biochemical assays.

Graphical abstract: Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization–oxidative Heck cascade and characterization as sirtuin modulators

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Publication details

The article was received on 27 Nov 2014, accepted on 06 Jan 2015 and first published on 06 Jan 2015


Article type: Paper
DOI: 10.1039/C4OB02493A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 2800-2810
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    Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization–oxidative Heck cascade and characterization as sirtuin modulators

    J. G. Denis, G. Franci, L. Altucci, J. M. Aurrecoechea, Á. R. de Lera and R. Álvarez, Org. Biomol. Chem., 2015, 13, 2800
    DOI: 10.1039/C4OB02493A

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