Three cascade reactions that provide access to various heterocyclic skeletons from quinols were developed. Firstly, the method for the creation of a variety of substituted 1-hydroxyacridones was realized in a one-pot carbamation/Michael addition/Claisen Condensation/decarboxylation sequence in good to excellent yields (41-96%). Secondly, such protocol was also applied to synthesize 4-hydroxyl pseudo-indoxyl derivatives using Lewis acid catalysis. Thirdly, the approach to construct substituted 4-hydoxycarbazoles was realized through a carbamation/Michael/palladium-catalysed enolate-aryl coupling/aromatization cascade. This methodology was also applied to a short total synthesis of carbazomycin B.

Heterocycle synthesis from quinols

253rd National Meeting (2017)

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