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Synthesis 1991; 1991(10): 871-878
DOI: 10.1055/s-1991-26597
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Preparation of Indoles and Oxindoles from N-(tert-Butoxycarbonyl)-2-alkylanilines

Robin D. Clark* , Joseph M. Muchowski, Lawrence E. Fisher, Lee A. Flippin, David B. Repke, Michel Souchet
  • *Syntex Research, Institute of Organic Chemistry, 3401 Hillview Ave., Palo Alto, CA 94304, USA
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Publication Date:
29 April 2002 (online)

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Treatment of dilithiated N-(tert-butoxycarbonyl)anilines 1 with dimethylformamide or carbon dioxide furnishes intermediates 3, 5, that are easily converted to N-(tert-butoxycarbonyl)indoles 4 and oxindoles (indol-2(3H)-ones, 7), respectively. Condensation of dilithiated 1 with N-methoxy-N-methylamides provides ketones 9 which are cyclized upon trifluoroacetic acid treatment to either 2-substituted 1-(tert-butoxycarbonyl)indoles 10 or 2-substituted indoles 11 depending on the reaction time. This general methodology has been applied to efficient synthesis of 1,2-alkyl-bridged indoles 12, 1,3,4,5-tetrahydrobenz[c,d]indole (16), 2a,3,4,5-tetrahydrobenz [c,d]indol-2(1H)-one (18), and 1-(tert-butoxycarbonyl) -1H-pyrrolo[2,3-b]pyridine (21).

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