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The Intramolecular Aromatic Electrophilic Substitution of Aminocyclopropanes Prepared by the Kulinkovich–de Meijere Reaction
Author(s) -
Larquetoux Laurent,
Ouhamou Nouara,
Chiaroni Angèle,
Six Yvan
Publication year - 2005
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.200500428
Subject(s) - chemistry , intramolecular force , electrophilic aromatic substitution , olefin fiber , moiety , ring (chemistry) , electrophilic substitution , electrophile , indole test , substitution reaction , phenol , medicinal chemistry , catalysis , organic chemistry
This article describes new examples of intramolecular Kulinkovich–de Meijere reactions applied to carboxylic amides bearing an olefin moiety and an aromatic ring at a suitable position. Upon heating, the aminocyclopropanes thus obtained undergo intramolecular aromatic electrophilic substitution to afford polycyclic systems. Among the various starting materials prepared, best results are obtained from indole and phenol derivatives. In each case, a benzylic quaternary centre is introduced at the newly‐formed ring junction. On one example, the efficiency of the cyclisation has been dramatically improved using a catalytic amount of para ‐toluenesulfonic acid. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)