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  • Title: Generation of N-(tert-butoxycarbonyl)indole-2,3-quinodimethane and its [4+2]-type cycloaddition.
    Author: Inagaki F, Mizutani M, Kuroda N, Mukai C.
    Journal: J Org Chem; 2009 Aug 21; 74(16):6402-5. PubMed ID: 19621889.
    Abstract:
    The two conditions for the preparation of the reactive N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane intermediate were developed by the reaction of the N-(tert-butoxycarbonyl)-2-(1-ethoxycarbonyloxymethylallenyl)aniline with K(2)CO(3) or Pd(2)(dba)(3) in refluxing toluene. The resulting N-(tert-butoxycarbonyl)indolo-2,3-quinodimethane was captured by several alkenyl and alkynyl dienophiles to provide the corresponding tetrahydro- and dihydrocarbazole derivatives.
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