An Expedient Flow Chemistry Approach to Substituted 1,4‐Dimethylcarbazoles

Abstract A simple, expedient continuously scalable flow chemistry synthesis of a range of 1,4‐dimethylcarbazoles from substituted indoles and 2,5‐hexanedione in the presence of K‐10 (montmorillonite clay) is reported. Optimization of the flow conditions led to the development of an in‐house K‐10/sand Omnifit TM catalyst column that at 140 °C and 0.4 mL.min −1 afforded >90% conversion of the selected indole to the desired 1,4‐carbazole. This equates to a ca 80 mg.h −1 production rate. The reaction was tolerant of electron donating indoles but not electron withdrawing indoles.

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Publication Details

Journal
ChemistrySelect
Published
2025-03-28
DOI
https://doi.org/10.1002/slct.202500249
Primary Topic
Synthesis and Biological Evaluation
Type
article
Field-Weighted Citation Impact
0.00

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article

An Expedient Flow Chemistry Approach to Substituted 1,4‐Dimethylcarbazoles

Adam McCluskey, Jennifer R. Baker, Cecilia C. Russell, Michael C. Hamilton et al.
ChemistrySelect
Synthesis and Biological Evaluation
article

An Expedient Flow Chemistry Approach to Substituted 1,4‐Dimethylcarbazoles

Adam McCluskey, Jennifer R. Baker, Cecilia C. Russell, Michael C. Hamilton, Fiona M. Deane, Louis E Matheson
article en

Abstract

Abstract A simple, expedient continuously scalable flow chemistry synthesis of a range of 1,4‐dimethylcarbazoles from substituted indoles and 2,5‐hexanedione in the presence of K‐10 (montmorillonite clay) is reported. Optimization of the flow conditions led to the development of an in‐house K‐10/sand Omnifit TM catalyst column that at 140 °C and 0.4 mL.min −1 afforded >90% conversion of the selected indole to the desired 1,4‐carbazole. This equates to a ca 80 mg.h −1 production rate. The reaction was tolerant of electron donating indoles but not electron withdrawing indoles.

ChemistrySelectVol. 10(13)
University of Newcastle Australia (AU)
Ramaciotti Foundations, Australian Cancer Research Foundation, Australian Research Council
Openalex Percentile: Top 95%
Synthesis and Biological Evaluation
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