- One-pot ring-closing metathesis/1,3-dipolar cycloaddition through assisted tandem ruthenium catalysis: Synthesis of a dye with isoindolo[2,1-a]quinoline structure
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The one-pot tandem reaction of N-alkyl-N-allyl-2-vinylaniline derivatives with benzo- or naphthoquinones and a ruthenium-alkylidene catalyst leads to isoindolo[2,1-a]quinolines in a variety of colors, which can be altered by exchanging the substituent on the core heterocycle (see scheme). This reaction offers a new synthetic method for π-conjugated small molecules from simple aniline derivatives. Copyright
- Arisawa, Mitsuhiro,Fujii, Yuki,Kato, Hiroshige,Fukuda, Hayato,Matsumoto, Takashi,Ito, Mika,Abe, Hiroshi,Ito, Yoshihiro,Shuto, Satoshi
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p. 1003 - 1007
(2013/03/13)
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- A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents
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A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2- dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology.
- Theeraladanon, Chumpol,Arisawa, Mitsuhiro,Nishida, Atsushi,Nakagawa, Masako
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p. 3017 - 3035
(2007/10/03)
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