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Synthesis 2005(12): 2029-2038  
DOI: 10.1055/s-2005-870003
PAPER
© Georg Thieme Verlag Stuttgart · New York

Sequential Three-Component and Heck Reactions for the Synthesis of Phenanthridones

Axel Jacobi von Wangelina, Helfried Neumanna, Dirk Gördesa, Sandra Hübnera, Christian Wendlerb, Stefan Klausa, Dirk Strübinga, Anke Spannenberga, Haijun Jiaoa, Larbi El Firdoussic, Kerstin Thurowb, Norbert Stollb, Matthias Beller*a
a Leibniz-Institute für Organische Katalyse, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Fax: +49(381)4669324; e-Mail: matthias.beller@ifok.uni-rostock.de;
b Institut für Automatisierungstechnik, Universität Rostock, Richard-Wagner-Str. 31, 18119 Rostock, Germany
c Laboratoire de Chimie de Coordination, Faculté des Sciences Semlalia, BP 2390 Marrakech, Morocco
Further Information

Publication History

Received 31 January 2005
Publication Date:
14 July 2005 (online)

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Abstract

A condensation-cycloaddition-cross-coupling reaction sequence has been applied to the synthesis of phenanthridone derivatives. This novel two-step procedure is based on a three-component reaction to give 2-halobenzamide-substituted cyclohexenes, which undergo palladium-catalyzed intramolecular Heck cyclizations.

Key words

domino reactions - Heck reactions - isomerizations - heterocycles - palladium

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13

See also Supporting Information of ref. 5a.

14

Suitable crystals of 10a were obtained by recrystallization from toluene-EtOAc (10:1).

15

X-ray data of 10a were collected with a STOE-IPDS diffractometer using graphite-monochromated Mo-K α radiation (λ = 0.71069 Å). The structure was solved by direct methods [16a] and refined by full matrix least square techniques against F ² . [16b] XP (Bruker AXS) was used for structure representation. All non-hydrogen atoms were refined anisotropically. The hydrogen atoms (except NH) were included at calculated positions and refined by the riding model. Crystal data for 10a: space group Pna21, orthorhombic, a = 13.328 (3), b = 9.314 (2), c = 18.207 (4) Å, V = 2260.2 (9) Å3, Z = 8, ρcalcd = 1.318 g cm-3, 11205 reflections measured, 3580 were independent of symmetry and 2524 were observed [I > 2σ (I)], R1 = 0.043, wR2 (all data) = 0.091, 315 parameters.