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Beilstein J. Org. Chem. 2014, 10, 2186–2199, doi:10.3762/bjoc.10.226
Graphical Abstract
Figure 1: General structures of biologically active dihydroisoquinolines, THIQs and 1,2-diarylindoles.
Scheme 1: Li’s THIQ indolation protocol.
Scheme 2: Possible strategies for the synthesis of target structure 1. Dashed arrows indicate literature-know...
Scheme 3: Nucleophilic substitution of DMEDA with 2-fluoro-3-iodopyridine (10).
Scheme 4: Decomposition of 1-(indol-3-yl)-THIQ 4d during N-arylation (monitored by GC–MS).
Scheme 5: Formation of byproduct 13 via benzylic oxidation.
Scheme 6: Routes towards 1,2-diarylindoles starting from indole; a: PhB(OH)2 (3 equiv), Pd(OAc)2 (5 mol %), A...
Scheme 7: Palladium-catalyzed C2-arylation attempt of 1-(1-phenylindol-3-yl)-N-Boc-THIQ.