title: One-pot synthesis of dibenzo[b,h][1,6]naphthyridines from 2-acetylaminobenzaldehyde: application to a fluorescent DNA-binding compound.
abstract: Dibenzo[b,h][1,6]naphthyridines were synthesized in one pot by reacting 2-acetylaminobenzaldehyde with methyl ketones under basic conditions via four sequential condensation reactions. This method was also applied to the synthesis of 1,2-dihydroquinolines. 6-Methyl-1,6-dibenzonaphthyridinium triflates showed strong fluorescence, and the fluorescence intensities were changed upon intercalation into double-stranded DNA.
authors.affiliation: Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan. kokuma@fukuoka-u.ac.jp.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Okuma
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Koga
authors.forename: Saori
authors.initials: S
authors.lastname: Ozaki
authors.forename: Yutaro
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Kenta
authors.initials: K
authors.lastname: Horigami
authors.forename: Noriyoshi
authors.initials: N
authors.lastname: Nagahora
authors.forename: Kosei
authors.initials: K
authors.lastname: Shioji
authors.forename: Masatora
authors.initials: M
authors.lastname: Fukuda
authors.forename: Masanobu
authors.initials: M
authors.lastname: Deshimaru
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C544515:1,4-dihydroquinoline; D001547:Benzaldehydes; D005456:Fluorescent Dyes; D007364:Intercalating Agents; D007659:Ketones; D009287:Naphthyridines; D011804:Quinolines; D004247:DNA