title: Platinum-Catalyzed Friedel-Crafts-Type C-H Coupling-Allylic Amination Cascade to Synthesize 3,4-Fused Tricyclic Indoles.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Suzuki
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.
authors.forename: Yuito
authors.initials: Y
authors.lastname: Tanaka
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.
authors.forename: Shun-ichi
authors.initials: S
authors.lastname: Nakano
authors.affiliation: Synthetic Organic Chemistry Laboratory, RIKEN, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan.
authors.forename: Kosuke
authors.initials: K
authors.lastname: Dodo
authors.affiliation: Graduate School of Medicine, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8670, Japan.
authors.forename: Natsumi
authors.initials: N
authors.lastname: Yoda
authors.affiliation: Graduate School of Medicine, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8670, Japan.
authors.forename: Ken-Ichi
authors.initials: K
authors.lastname: Shinohara
authors.affiliation: Graduate School of Medicine, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8670, Japan.
authors.forename: Kazuko
authors.initials: K
authors.lastname: Kita
authors.affiliation: Graduate School of Medicine, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8670, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kaneda
authors.affiliation: Synthetic Organic Chemistry Laboratory, RIKEN, 2-1, Hirosawa, Wako, Saitama, 351-0198, Japan.
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Hamada
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan. tnemoto@faculty.chiba-u.jp.|Molecular Chirality Research Center, Chiba University, 1-33, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan. tnemoto@faculty.chiba-u.jp.
authors.forename: Tetsuhiro
authors.initials: T
authors.lastname: Nemoto
mesh_terms: D000586:Amination; D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D007211:Indoles; D010984:Platinum
keywords: C−H activation; antitumor agents; cascade reactions; heterocycles; platinum