Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 9, Pages 1463-1467Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob27493d
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Funding
- Center of Excellence on Environmental Health and Toxicology, Science and Technology Postgraduate Education and Research Development Office (PERDO), Ministry of Education, Chulabhorn Research Institute
- Thailand Research Fund [TRG558008]
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A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.
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