title: Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines.
abstract: Reaction of 6-arylamino-1,3-dialkyluracils with anhydrides of polyfluorocarboxylic acids in the presence of pyridine and subsequent cyclization with concentrated H2SO4 gave the corresponding 1,3-dialkyl-5-(polyfluoroalkyl)pyrimido[4,5-b]quinoline-2,4(1H,3H)-diones (5-polyfluoroalkyl-5-deazaalloxazines). The reactivity of these compounds towards nucleophilic reagents, such as sodium cyanoborohydride, acetophenone, nitromethane, potassium cyanide, indole and p-thiocresol, as well as Suzuki and Sonogashira couplings are described. The nucleophilic addition takes place at the 5-position of the 5-deazaalloxazine system and is in many cases irreversible to give 5,10-dihydropyrimido[4,5-b]quinoline-2,4(1H,3H)-dione derivatives in good to excellent yields.
authors.affiliation: Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany.
authors.forename: Sergii
authors.initials: S
authors.lastname: Dudkin
authors.forename: Viktor O
authors.initials: VO
authors.lastname: Iaroshenko
authors.forename: Vyacheslav Ya
authors.initials: VY
authors.lastname: Sosnovskikh
authors.forename: Andrey A
authors.initials: AA
authors.lastname: Tolmachev
authors.forename: Alexander
authors.initials: A
authors.lastname: Villinger
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D000478:Alkylation; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005415:Flavins / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D011725:Pyridines / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000031:analogs & derivatives
chemical_list: D001372:Aza Compounds; D005415:Flavins; D011725:Pyridines; D011804:Quinolines; C008173:isoalloxazine; D014498:Uracil; C023666:pyridine