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Acid‐Free Synthesis of Carbazoles and Carbazolequinones by Intramolecular Pd‐Catalyzed, Microwave‐Assisted Oxidative Biaryl Coupling Reactions – Efficient Syntheses of Murrayafoline A, 2‐Methoxy‐3‐methylcarbazole, and Glycozolidine
Author(s) -
Sridharan Vellaisamy,
Martín M. Antonia,
Menéndez J. Carlos
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900537
Subject(s) - chemistry , intramolecular force , oxidative coupling of methane , catalysis , oxidative phosphorylation , combinatorial chemistry , organic chemistry , coupling (piping) , microwave chemistry , coupling reaction , microwave irradiation , stereochemistry , biochemistry , mechanical engineering , engineering
A mild and efficient methodology for the synthesis of oxygenated carbazoles from diarylamines under non‐acidic conditions was developed, based on a palladium‐catalyzed, microwave‐assisted double C–H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2‐methoxy‐3‐methylcarbazole, and glycozolidine. The scope of the reaction was also expanded to include the synthesis of benzo fused carbazolequinones.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)