Regioselective dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones mediated by ceric ammonium nitrate

被引：49
作者：
Shanmugam, P. [1 ]
Perumal, P. T. [1 ]
机构：
[1] Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India
来源：
TETRAHEDRON | 2006年 / 62卷 / 41期
关键词：
oxidation; pyrimidines; 3,4-dihydropyrimidin-2(1H)-ones; ceric ammonium nitrate;
D O I：
10.1016/j.tet.2006.07.063
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ceric ammonium nitrate (CAN) has been explored for the regioselective oxidation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs). Interestingly, we obtained ethyl 2,4-dioxo-6-phenyl-tetrahydropyrimidin-5-carboxylates as the major products during the oxidation of DHPMs by CAN/AcOH at 80 degrees C. The reaction afforded a mixture of products while employing CAN in organic solvents without additives. However, the regioselective dehydrogenated product, ethyl 6-methyl-4-aryl(alkyl)-pyrimidin-2(1H)-one-5-carboxylate was obtained by performing the reaction with NaHCO3. The single crystal X-ray crystallography of ethyl 6-methyl-4-(2-phenyl)-pyrimidin-2(1H)-one-5-carboxylate revealed that the oxidized product existed in amidic form rather than aromatized enol form of pyrimidines. The efficiency of the present protocol enabled the synthesis of structurally diverse pyrimidines in moderate to good yields under milder reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9726 / 9734
页数：9
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