title: Development of an Enyne Metathesis/Isomerization/Diels-Alder One-Pot Reaction for the Synthesis of a Novel Near-Infrared (NIR) Dye Core.
abstract: N-Alkyl-N-allyl-2-alkynylaniline derivatives undergo a tandem ring-closing enyne metathesis/isomerization/Diels-Alder cycloaddition sequence in the presence of a second-generation Grubbs catalyst and dienophiles. In practice, the acyclic enyne in the presence of the ruthenium alkylidene first undergoes ring-closing metathesis to generate cyclic 4-vinyl-1,2-dihydroquinolines; following diene isomerization and then the addition of a dienophile, these ring-closing metathesis products are selectively converted into a 7-methyl-4H-naphtho[3,2,1-de]quinoline-8,11-dione core. Overall, the reaction sequence converts simple aniline derivatives into π-conjugated small molecules, which have characteristic absorption in the near-infrared region, in a single operation through three unique ruthenium-catalyzed transformations.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Kohei
authors.initials: K
authors.lastname: Yamashita
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Yuki
authors.initials: Y
authors.lastname: Fujii
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Shohei
authors.initials: S
authors.lastname: Yoshioka
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Aoyama
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Tsujino
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Tadayuki
authors.initials: T
authors.lastname: Uno
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan).
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Fujioka
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871 (Japan). arisaw@phs.osaka-u.ac.jp.
authors.forename: Mitsuhiro
authors.initials: M
authors.lastname: Arisawa
keywords: cycloaddition; domino reactions; dyes/pigments; heterocycles; metathesis