Synthesis and reactivity of 5-polyfluoroalkyl-5-deazaalloxazines

被引:19
|
作者
Dudkin, Sergii [1 ]
Iaroshenko, Viktor O. [1 ,2 ]
Sosnovskikh, Vyacheslav Ya [3 ]
Tolmachev, Andrey A. [2 ,4 ]
Villinger, Alexander [1 ]
Langer, Peter [1 ,5 ]
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine
[3] Ural Fed Univ, Dept Chem, Ekaterinburg 620000, Russia
[4] Enamine Ltd, UA-01103 Kiev, Ukraine
[5] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
ADENOSINE-DEAMINASE; OXIDATIVE CYCLIZATION; CONVENIENT SYNTHESIS; 5-DEAZAFLAVINS; NUCLEOPHILES; FACILE; PURINE;
D O I
10.1039/c3ob26837c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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-(polyfluoroakyl)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.
引用
收藏
页码:5351 / 5361
页数:11
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