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Issue 5, 2019
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Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals

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Abstract

The direct and rapid construction of carbazoles was achieved via the reaction of 2-methyl-indole-3-carbaldehydes with enals promoted by LiCl/DBU in a single operation. This mild and green reaction proceeds through a [4 + 2] cycloaddition/dehydration/oxidative aromatization cascade to generate carbazoles in good to excellent yields. The reaction features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, using O2 (1 atm) as the sole oxidant and affording H2O as the only by-product. More importantly, 4-fluoroquinocarbazole, a significant bioactive compound, was generated in 80% yield in only one step from the obtained carbazole.

Graphical abstract: Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals

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Article information


Submitted
08 Jan 2019
Accepted
31 Jan 2019
First published
31 Jan 2019

Green Chem., 2019,21, 968-972
Article type
Communication

Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals

D. Liu, J. Huang, Z. Fu and W. Huang, Green Chem., 2019, 21, 968
DOI: 10.1039/C9GC00064J

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