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SYNTHESIS OF 1,2,6-TRISUBSTITUTED INDOLES FROM 6-PROPARGYLCYCLOHEX-2-ENONES AND PRIMARY AMINES

Sergei G. Mikhalyonok, Nina M. Kuz'menok, Vladimir S. Bezborodov, Aliaksandr S. Arol
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Abstract


The synthesis of 1,2,6-trisubstituted indoles from accessible 6-propargylcyclohex-2-enones and primary amines is reported. Simple acidcatalyzed amination–cyclization reaction followed by air oxidation of the corresponding intermediated 4,5-dihydroindoles was found to be suitable to obtain the desired indoles. The reaction tolerates a variety of functional groups on the starting cyclohex-2-enones and primary amines. A mechanistic pathway involving nucleophilic addition/cyclization/aromatization is proposed.

Keywords


cyclohex-2-enone; indole; air oxidation; amination–cyclization reaction

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