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Platinum‐Catalyzed Friedel–Crafts‐Type C−H Coupling–Allylic Amination Cascade to Synthesize 3,4‐Fused Tricyclic Indoles
Author(s) -
Suzuki Yuta,
Tanaka Yuito,
Nakano Shunichi,
Dodo Kosuke,
Yoda Natsumi,
Shinohara Kenichi,
Kita Kazuko,
Kaneda Atsushi,
Sodeoka Mikiko,
Hamada Yasumasa,
Nemoto Tetsuhiro
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600375
Subject(s) - amination , chemistry , aniline , allylic rearrangement , catalysis , friedel–crafts reaction , trifluoroacetic acid , intramolecular force , indole test , propargyl , medicinal chemistry , coupling reaction , tricyclic , palladium , combinatorial chemistry , organic chemistry
A novel platinum‐catalyzed cascade cyclization reaction was developed by intramolecular Friedel–Crafts‐type C−H coupling of aniline derivatives with a propargyl carbonate unit‐allylic amination sequence. Treatment of various propargyl carbonates tethered to meta‐ aniline derivatives with a Pt(dba) 3 /DPEphos catalyst system afforded the corresponding 3,4‐fused tricyclic 3‐alkylidene indolines in 42–99 % yield, which were transformed into 3,4‐fused indole derivatives by reaction with trifluoroacetic acid. The reaction products exhibited antiproliferative activities against cancer cells, but not normal cells, revealing the potential usefulness of this reaction for medicinal chemistry.