Synthesis

Transition Metal-Diene Complexes in Organic Synthesis, Part 22. The Iron-Mediated Quinone Imine Cyclization: A General Route to 3-Hydroxycarbazoles

HJ Knölker, M Bauermeister, JB Pannek, M Wolpert

Index: Knolker; Bauermeister; Pannek; Wolpert Synthesis, 1995 , # 4 p. 397 - 408

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Citation Number: 29

Abstract

Electrophilic aromatic substitution of 4-methoxyarylamines 2 by the tricarbonyliron- complexed cyclohexadienylium cations 1 leading to the iron complexes 3 is described. Chemoselective oxidation of the arylamine moiety of the complexes 3 to the quinone imine and iron-mediated quinone imine cyclization using appropriate oxidizing reagents (activated manganese dioxide or thallium (III) triﬂuoroacetate) led to the tricarbonyliron-complexed ...

~99%

~39%

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