One-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions |
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Authors: | Adisak Thanetchaiyakup Hassayaporn Rattanarat Nutthawat Chuanopparat Paiboon Ngernmeesri |
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Affiliation: | Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, and Special Research Unit for Advanced Magnetic Resonance (AMR), Kasetsart University, Bangkok 10900, Thailand |
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Abstract: | A simple and efficient one-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions has been developed. When 2-fluorobenzaldehyde was treated with substituted 2-methylindoles in the presence of Cs2CO3, the desired products were typically obtained in good to excellent yields. This reaction sequence involves a nucleophilic aromatic substitution and a Knoevenagel condensation reaction. Our mechanistic investigation revealed that both reactions could proceed as an intermolecular reaction in the first step. |
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Keywords: | One-pot synthesis Transition-metal-free synthesis Nucleophilic aromatic substitution Knoevenagel condensation |
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