Journal
TETRAHEDRON LETTERS
Volume 59, Issue 11, Pages 1014-1018Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2018.01.085
Keywords
One-pot synthesis; Transition-metal-free synthesis; Indolo[1,2-a]quinoline; Nucleophilic aromatic substitution; Knoevenagel condensation
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Funding
- Kasetsart University Research and Development Institute (KURDI)
- Thailand Research Fund [DBG5480018]
- Center of Excellence for Innovation in Chemistry (PERCH-CIC)
- Commission on Higher Education (CHE)
- Ministry of Education, the Department of Chemistry
- Faculty of Science, Kasetsart University
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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. (C) 2018 Elsevier Ltd. All rights reserved.
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