Syntheses of Hydrocarbazole Derivatives via Brønsted acid-Initiated Diels-Alder Cycloaddition/retro-Michael Addition Cascade Reaction of Azepino[4,5-b]indoles and Acrolein

23 June 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A unique approach to hydrocarbazoles bearing an all-carbon quaternary center at C4a position was developed via a Brønsted acid-initiated Diels-Alder cycloaddition/retro-Michael addition cascade process from facilely prepared azepino[4,5-b]indoles and commercially available acrolein. The method provided a range of hydrocarbazoles in good to excellent yields. The practi-cality of this transformation was demonstrated by scale-up experiment and various transformations to several hydrocarbazole derivatives.

Keywords

hydrocarbazole
Diels-Alder Cycloaddition
Brønsted Acid Catalysis

Supplementary materials

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Title
Syntheses of Hydrocarbazole Derivatives via Brønsted acid-Initiated Diels-Alder Cycloaddition/retro-Michael Addition Cascade Reaction of Azepino[4,5-b]indoles and Acrolein
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The supporting information of the paper entitled 'Syntheses of Hydrocarbazole Derivatives via Brønsted acid-Initiated Diels-Alder Cycloaddition/retro-Michael Addition Cascade Reaction of Azepino[4,5-b]indoles and Acrolein'
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