Carbanionic Friedel− Crafts Equivalents. Regioselective Directed Ortho and Remote Metalation− C− N Cross Coupling Routes to Acridones and Dibenzo [b, f] …

SL MacNeil, M Gray, DG Gusev, LE Briggs…

Index: MacNeil, Stephen L.; Gray, Matthew; Gusev, Dmitry G.; Briggs, Laura E.; Snieckus, Victor Journal of Organic Chemistry, 2008 , vol. 73, # 24 p. 9710 - 9719

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Citation Number: 30

Abstract

Carbanion-mediated general regioselective routes to acridones 4 (Table 2) and dibenzo [b, f] azepinones 20 (Table 4) are described. Buchwald− Hartwig C− N cross coupling of o-halo benzamides 1 with anilines 2 or 16, followed by simple N-methylation, dependably provides N-methyl diarylamines 3 (Table 1) and 18 (Table 3). Upon treatment with LDA, 3 and 18 are converted into acridones 4 and dibenzo [b, f] azepinones 20, respectively, in good to ...