Synthesis of Ethyl Pyrimidine-4-carboxylates from Unsymmetrical Enamino Diketones and Their Application in the First Synthesis of Pyrimido[4,5-d]pyridazin-8(7H)-ones

被引：13

作者：

Rosa, Fernanda A. ^{[1
]}

Machado, Pablo ^{[1
]}

Fiss, Gabriela F. ^{[1
]}

Vargas, Pamela S. ^{[1
]}

Fernandes, Tanize S. ^{[1
]}

Bonacorso, Helio G. ^{[1
]}

Zanatta, Nilo ^{[1
]}

Martins, Marcos A. P. ^{[1
]}

机构：

[1] Univ Fed Santa Maria, Dept Quim, NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil

来源：

SYNTHESIS-STUTTGART | 2008年 / 22期

关键词：

cyclizations; enones; ring closure; heterocycles; pyrimidines; regioselectivity;

D O I：

10.1055/s-0028-1083202

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of unsymmetrical enamino diketones [RC(O)C(=CNMe2)C(O)CO2Et, where R=Ph, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, 4-ClC6H4, 4-FC6-H-4, 4-O2NC6H4, 2-thienyl, benzofuran-2-yl, and CF3] with N-C-N dinucleophiles, such as benzamidine hydrochloride or 1H-pyrazole-1-carboxamidine monohydrochloride, afforded a series of ethyl 2,5-disubstituted pyrimidine-4-carboxylates in a chemoselective and highly chemoselective manner (51-86%). Reaction of these two series of pyrimidines (R = Ph, 4-MeOC6H4, 4-FC6H4, and 2-thienyl) with hydrazine monohydrate under mild conditions led to 2,5-substituted pyrimido[4,5-d]pyridazin-8(7H)-ones in high yields (81-92%).

引用

页码：3639 / 3648

页数：10

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