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
收藏
页码：3639 / 3648
页数：10
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