Abstract
The literature on the syntheses of substituted 1-(indol-3-yl)-1,2,3,4-tetrahydroisoquinoline derivatives is reviewed. Two main synthetic procedures have been applied for these syntheses. One is cross-dehydrogenative coupling, which can furnish various C-3 functionalized indoles; oxidants and/or catalysts are usually needed. Another convenient synthetic method is the aza-Friedel–Crafts alkylation of indole derivatives with dihydroisoquinoline, the main advantage of this being the direct catalyst-free coupling under mild experimental conditions. The review also considers miscellaneous reactions, where the isoquinoline skeleton is achieved in one of the final steps of the synthesis.
Keywords: Isoquinoline, indole, β-carboline, cross-dehydrogenative coupling, aza-Friedel–Crafts alkylation.
Current Organic Chemistry
Title:C-3 Functionalization of Indole Derivatives with Isoquinolines
Volume: 20 Issue: 20
Author(s): István Szatmári, Judit Sas and Ferenc Fülöp
Affiliation:
Keywords: Isoquinoline, indole, β-carboline, cross-dehydrogenative coupling, aza-Friedel–Crafts alkylation.
Abstract: The literature on the syntheses of substituted 1-(indol-3-yl)-1,2,3,4-tetrahydroisoquinoline derivatives is reviewed. Two main synthetic procedures have been applied for these syntheses. One is cross-dehydrogenative coupling, which can furnish various C-3 functionalized indoles; oxidants and/or catalysts are usually needed. Another convenient synthetic method is the aza-Friedel–Crafts alkylation of indole derivatives with dihydroisoquinoline, the main advantage of this being the direct catalyst-free coupling under mild experimental conditions. The review also considers miscellaneous reactions, where the isoquinoline skeleton is achieved in one of the final steps of the synthesis.
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Cite this article as:
Szatmári István, Sas Judit and Fülöp Ferenc, C-3 Functionalization of Indole Derivatives with Isoquinolines, Current Organic Chemistry 2016; 20 (20) . https://dx.doi.org/10.2174/1385272820666160325202857
DOI https://dx.doi.org/10.2174/1385272820666160325202857 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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