Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines

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.

Dudkin S.; Iaroshenko V. O.; Sosnovskikh V. Y.; Tolmachev A. A.; Villinger A.; Langer P.
Org. Biomol. Chem. 2013, 11 (32), 5351-5361
DOI: 10.1039/C3OB26837C