Zinc-catalyzed reactions of ethenetricarboxylates with 2-(trimethylsilylethynyl)anilines leading to bridged quinoline derivatives.
Zinc Lewis acid-catalyzed cyclization of ethenetricarboxylate derivatives 1 with 2-ethynylanilines has been examined. Reaction of 1,1-diethyl 2-tert-butyl ethenetricarboxylate 1b with 2-(trimethylsilylethynyl)aniline substrates in the presence of Zn(OTf)(2) gave bridged quinoline derivatives in 43-85% yield. The reaction of 1b with 2'-aminoacetophenone also gave the bridged quinoline derivative in 41% yield. Thermal reaction of bridged quinolines (180-190 degrees C) afforded indole derivatives in moderate to good yields.
Yamazaki
Shoko
S
Department of Chemistry, Nara University of Education, Takabatake-cho, Nara 630-8528, Japan. yamazaks@nara-edu.ac.jp
Morikawa
Satoshi
S
Miyazaki
Kazuya
K
Takebayashi
Masachika
M
Yamamoto
Yuko
Y
Morimoto
Tsumoru
T
Kakiuchi
Kiyomi
K
Mikata
Yuji
Y
D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D014233:Tricarboxylic Acids / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D000814:Aniline Compounds; D006572:Heterocyclic Compounds, Bridged-Ring; D007211:Indoles; D011804:Quinolines; D014233:Tricarboxylic Acids; D015032:Zinc