Issue 9, 2015
From the journal:

Organic & Biomolecular Chemistry

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,a   G. Franci,b   L. Altucci,b   J. M. Aurrecoechea,c   Á. R. de Lera*a  and  R. Álvarez*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Química (CINBIO) and Instituto de Investigación Biomédica de Vigo (IBIV), Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain
E-mail: rar@uvigo.es, qolera@uvigo.es
Fax: +34 986 811940
Tel: +34 986 812316

b Seconda Università degli Studi di Napoli, Dipartimento di Biochimica, Biofisica e Patologia generale, Vico L. De Crecchio 7, Napoli, Italy

c Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco, Apartado 644, 48080 Bilbao, Spain

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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Article information

DOI
https://doi.org/10.1039/C4OB02493A
Article type
Paper
Submitted
27 Nov 2014
Accepted
06 Jan 2015
First published
06 Jan 2015

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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