New synthesis of oxcarbazepine via remote metalation of protected No-tolyl-anthranilamide derivatives

O Lohse, U Beutler, P Fünfschilling, P Furet, J France…

Index: Lohse, Olivier; Beutler, Ulrich; Fuenfschilling, Peter; Furet, Pascal; France, Julien; Kaufmann, Daniel; Penn, Gerhard; Zaugg, Werner Tetrahedron Letters, 2001 , vol. 42, # 3 p. 385 - 389

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Citation Number: 37

Abstract

Benzyl and allyl protected No-tolyl-anthranilamides were efficiently prepared by Buchwald– Hartwig C–N cross coupling reactions, followed by protection of the amino group. Under directed remote metalation conditions, protected dibenzoazepinones were obtained in good yields. Deprotection of the amine and conversion to an urea furnished a new and efficient synthesis of the antiepileptic drug Trileptal®.