Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 9, Pages 4516-4525Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00375
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Funding
- Chulabhorn Research Institute
- Mahidol University
- Thailand Research Fund [TRG558008]
- Center of Excellence on Environmental Health and Toxicology, Science & Technology Postgraduate Education and Research Development Office (PERDO), Ministry of Education
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Regioselective synthesis of 3-bromoquinoline derivatives was achieved via a formal [4 + 2]-cycloaddition between N-aryliminium ion, generated from arylmethyl azides, and 1-bromoalkynes. This method could also be applied to other quinoline derivatives using appropriate alkynes. Moreover, the current strategy could be utilized for the diastereoselective synthesis of tetrahydroquinoline derivatives employing alkenyl substrates in good to excellent yields.
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