Efficient Synthesis of Arylated Flavones by Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of the Bis(triflate) of 5,7-and 7,8-Dihydroxyflavone

被引：16

作者：

Eleya, Nadi ^{[1
]}

Malik, Imran ^{[1
,2
]}

Reimann, Sebastian ^{[1
,3
]}

Wittler, Kai ^{[4
]}

Hein, Martin ^{[1
]}

Patonay, Tamas ^{[2
]}

Villinger, Alexander ^{[1
]}

Ludwig, Ralf ^{[3
,4
]}

Langer, Peter ^{[1
,3
]}

机构：

[1] Univ Rostock, Dept Chem, D-18059 Rostock, Germany

[2] Univ Debrecen, Dept Organ Chem, H-4032 Debrecen, Hungary

[3] Univ Rostock eV LIKAT, Leibniz Inst Catalysis, D-18059 Rostock, Germany

[4] Univ Rostock, Dept Chem Phys & Theoret Chem, D-18059 Rostock, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 08期

关键词：

Synthetic methods; Natural products; Heterocycles; Flavones; Cross-coupling; Palladium; Regioselectivity; 1ST TOTAL-SYNTHESIS; N-OXIDES; DERIVATIVES; FLAVANONES; ROUTE; DEHYDROGENATION; INHIBITORS; OXIDATION; CHROMONES; 2'-HYDROXYCHALCONES;

D O I：

10.1002/ejoc.201101491

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suzuki-Miyaura reactions of the bis(triflate) of 5,7- and 7,8-dihydroxyflavone proceed with very good site selectivity in favor of position 7 and allow the synthesis of various arylated flavones. The reaction of 5,7-dihydroxyflavone with one equivalent of triflic anhydride also proceeds with very good site selectivity in favor of position 7. The subsequent Suzuki-Miyaura reaction of the product allows the synthesis of 7-aryl-5-hydroxyflavones. The regioselectivity is discussed based on DFT calculations.

引用

页码：1639 / 1652

页数：14

共 71 条

[61] Lead optimization of 7-benzyloxy 2-(4′-pyridylmethyl)thio isoflavone aromatase inhibitors [J].