A Brønsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α‐(3‐Indolyl) Ketones by Using 2‐Benzyloxy Aldehydes

作者: Ankush Banerjee , Modhu Sudan Maji

DOI: 10.1002/CHEM.201902268

关键词: AnnulationCatalysisChemistryReagentCombinatorial chemistryCascade reactionReaction intermediateIndole testBrønsted–Lowry acid–base theoryPyrrole

摘要: A Bronsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue eliminated by choosing appropriate carbonyls. readily available cheap bottle reagent was used as catalyst. This protocol also applicable synthesis of densely α-(3-pyrrolyl) ketones. detailed mechanistic study confirmed involvement enolether a reaction intermediate. Several postsynthetic modifications along with easy access β-carboline, tryptamines, tryptophols, spiro-indolenine proclaim synthetic utility this powerful building block. On basis concept, carbazoles were constructed cascade annulation strategy.

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