A condition-tuned unorthodox approach to indole-3-carboxylic acids and anthranilic acids via carbon atom translocation

Literature Information

Publication Date 2023-10-31
DOI 10.1039/D3CC04443B
Impact Factor 6.222
Authors

Arup Bhowmik, Koushik Naskar, Shantonu Roy, Sudip Karmakar, Writhabrata Sarkar, Imtiaj Mondal, Arindam Sana, Indubhusan Deb


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Abstract

We describe a robust one-pot cascade method for the synthesis of indole-3-carboxylic acids using isatins and DMSO via a one-carbon translocation involving in situ generation of α,β-unsaturated methylvinylsulfoxide followed by amide bond cleavage and ring closure. The methodology has been extended to afford anthranilic acid derivatives by tuning the reaction conditions in the presence of molecular oxygen. Importantly, easy access to commercially available drugs, including tropisetron, is demonstrated.

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Chemical Communications

Chemical Communications
CiteScore: 8.6
Self-citation Rate: 4.7%
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ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

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