Journal
TETRAHEDRON
Volume 70, Issue 12, Pages 2151-2160Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.01.074
Keywords
Cascade reaction; ipso-Friedel-Crafts alkylation; iso-Pictet-Spengler reaction; Indoloazepine; Tetrahydro-gamma-carboline
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- Research Foundation for Pharmaceutical Sciences
- JSPS
- Uehara Memorial Foundation
- Chiba University
- Grants-in-Aid for Scientific Research [23390003, 13J04207] Funding Source: KAKEN
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We developed a novel method for synthesizing fused-tricyclic indole derivatives with a 3-aminomethyl indole motif through a reaction cascade involving ipso-Friedel-Crafts alkylation of phenols, rearomatization of the spirocyclohexadienone unit, and iso-Pictet-Spengler reaction. Using TFA as an acid promoter, six-, seven-, and eight-membered ring-fused indoles were obtained in 31-99% yield. (C) 2014 Elsevier Ltd. All rights reserved.
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