Efficient and Simple Synthesis of 6-Aryl-1,4-dimethyl-9H-carbazoles.docVIP

Molecules 2008, 13, 1312-1320; DOI: 10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /molecules Article Efficient and Simple Synthesis of 6-Aryl-1,4-dimethyl-9H-carbazoles Anna Caruso 1,2, Anne Sophie Voisin-Chiret 1, Jean-Charles Lancelot 1, Maria Stefania Sinicropi 2, Antonio Garofalo 2 and Sylvain Rault 1,* 1 Université de Caen Basse-Normandie, U.F.R. des Sciences Pharmaceutiques, Centre d’Etudes et de Recherche sur le Médicament de Normandie, UPRES EA-4258 FR CNRS INC3M, 5, rue Vaubénard, 14032 Caen Cedex, France 2 Università della Calabria, Dipartimento di Scienze Farmaceutiche, 87036 Arcavacata di Rende (CS), Italy * Author to whom correspondence should be addressed; E-mail: sylvain.rault@unicaen.fr; Tel: +33 (0)2 31 93 64 58; Fax: +33 (0)2 31 93 11 88 Received: 3 June 2008; in revised form: 10 June 2008 / Accepted: 10 June 2008 / Published: 11 June 2008 Abstract: A synthetic method for the preparation of 6-aryl-1,4-dimethyl-9H-carbazoles involving a palladium catalyzed coupling reaction of 1,4-dimethyl-9H-carbazole-6-boronic acids and (hetero)aryl halides is described. Keywords: Carbazole, ellipticine, boronic acid, cross-coupling reaction. Introduction Several alkaloids based on a carbazole structure are known to possess interesting biological activities. Antitumor, antibacterial, anti-inflammatory, psychotropic and anti-histamine properties have been attributed to many of such compounds [1]. More recently, carbazoles have also been used as photoconductors, semiconductors and for their light-emitting properties, making them interesting organic tools for physics experiments [2]. The introduction of functional groups onto the carbazole scaffold is essential to generate compounds suitable for biological and physical investigations.  Molecules 2008, 13 1313 Standard electrophilic substitution reactions on readily available 1,4-dimethyl-9H-carbazoles are usually uns