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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 32期

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

页码：5351 / 5361

页数：11

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