Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 9, Pages 3866-3875Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo500308y
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- JSPS
- Uehara Memorial Foundation
- Chiba University
- Grants-in-Aid for Scientific Research [23390003, 26105707] Funding Source: KAKEN
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Two different cascade cyclization processes were developed using aryl group-substituted propargyl alcohol derivatives with a p-hydroxybenzylamine unit as common substrates. Using TFA as an acid promoter, an intramolecular ipso-Friedel-Crafts alkylation of phenol derivatives, formation of an iminium cation via a rearomatization-promoted C-C bond cleavage, an aza-Prins reaction, and a 6-membered ring formation proceeded sequentially, producing a variety of fused-tricyclic dihydroquinoline derivatives in 45-99% yield. In addition, a one-pot sequential silver acetate-catalyzed hydroamination/etherification-acid-promoted skeletal rearrangement was examined using the same series of substrates, affording fused-tricyclic indole/benzofuran derivatives in 66-89% yield.
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