Synthetic methods involving chemoselective tandem reactions for the synthesis of α-naphthylamines and indeno[1,2-c]pyrrolones starting from (o-aklynyl)phenyl enaminones are described. When reactions were carried out in N,N-dimethylformamide (DMF) using a AgNO catalyst, α-naphthylamines were obtained in up to 89% isolated yields within 2 h. Whereas indeno[1,2-c]pyrrolones were produced in high isolated yields in the presence of benzoyl peroxide (BPO) and CuCl catalysis.
A copper-catalyzed oxidative dearomatization/spirocyclization of indole-2-carboxamides using tert-butyl hydroperoxide (TBHP) as the oxidant has been developed that provides rapid and efficient access to C2-spiro-pseudoindoxyls. Two of the sp C-H bonds are functionalized during the reaction process, and the reaction likely proceeds via the formation of a highly reactive 3H-indol-3-one intermediate followed by aromatic electrophilic substitution with the N-aryl ring of the amide moiety.
An efficient and atom-economical methodology for the synthesis of multi-substituted carbazoles starting from α-aryl ketones and ynones under mild reaction conditions has been developed. This process goes through Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by highly selective C-H bond activations and C-C bond fragmentations in a one-pot operation.
A highly efficient ZnCl2-catalyzed cascade reaction of enaminones with 2-furylcarbinols under mild reaction conditions has been developed. This methodology offers a chemo- and diastereo-selective access to functionalized cyclopenta[b]pyrrole derivatives in good to excellent yields.
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