Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 12, Pages 8062-8073Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00893
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Funding
- Department of Science and Technology-Science and Engineering Research Board, DST-SERB [EMR/2016/001619, EMR/2016/002485]
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A sequential three-component cascade process was developed for the synthesis of bridged tetrahydroquinolines and chromanes bearing 2,6-methanobenzo[d][1,3]diazocine and 2,6-methanobenzo[g][1,3]oxazocine scaffolds, respectively, in good yields from readily available materials. The InCl3-catalyzed reaction progressed via enamine formation, Michael addition, intramolecular cyclization, and intramolecular iminium ion cyclization steps. Notably, this high atom economic approach (-2H(2)O) allowed the generation of four new bonds (1 C-C and 3 C-N or 1 C-C, 1 C-O and 2 C-N) and two heterocyclic rings in a single operation.
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