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Issue 32, 2013
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Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines

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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.

Graphical abstract: Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines

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Article information


Submitted
19 Sep 2012
Accepted
13 Jun 2013
First published
14 Jun 2013

Org. Biomol. Chem., 2013,11, 5351-5361
Article type
Paper

Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines

S. Dudkin, V. O. Iaroshenko, V. Ya. Sosnovskikh, A. A. Tolmachev, A. Villinger and P. Langer, Org. Biomol. Chem., 2013, 11, 5351
DOI: 10.1039/C3OB26837C

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