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Org Biomol Chem. 2013 Aug 28;11(32):5351-61. doi: 10.1039/c3ob26837c.

Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines.

Author information

1
Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany.

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.

PMID:
23846251
DOI:
10.1039/c3ob26837c
[Indexed for MEDLINE]

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