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Facile synthesis of some new functionalized 2-selenoxopyrimidines
Phosphorus, Sulfur, and Silicon and the Related Elements ( IF 1.4 ) Pub Date : 2019-11-23 , DOI: 10.1080/10426507.2019.1694023
Ahmed M. Fouda 1 , Mohammed A. Assiri 1 , Tarik E. Ali 1
Affiliation  

Abstract Some new functionalized 2-selenoxodihydropyrimidines 1–6 were synthesized in good yields via a simple one-pot reaction. The simple method depended on the reaction of selenourea with some nitrile active methylene compounds under basic-catalyzed conditions. Also, treatment of selenourea with each of malononitrile and ethyl cyanoacetate in the presence of benzaldehyde under the same basic reaction conditions afforded the 2-selenoxopyrimidine-5-carbonitriles 7 and 8, respectively. Furthermore, selenourea reacted with benzaldehyde and different β-dicarbonyl compounds under Biginelli reaction conditions to afford the 2-selenoxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 10, 11 and 13. Using acetylacetone as a substrate in Biginelli reaction yielded the unexpected 5-benzylidene-4,6-dimethyl-pyrimidine-2(5H)-selenone (14). The structures of the synthesized compounds were established on the basis of elemental analysis, IR, 1H- and 13C-NMR and mass spectral data. Graphical Abstract

中文翻译:

一些新功能化的 2-硒氧嘧啶的简单合成

摘要 通过简单的一锅反应以良好的收率合成了一些新的功能化 2-硒氧二氢嘧啶 1-6。这种简单的方法依赖于硒脲与一些腈类活性亚甲基化合物在碱性催化条件下的反应。此外,在苯甲醛的存在下,在相同的碱性反应条件下,用丙二腈和氰基乙酸乙酯分别处理硒脲,分别得到 2-硒代嘧啶-5-甲腈 7 和 8。此外,硒脲在 Biginelli 反应条件下与苯甲醛和不同的 β-二羰基化合物反应,得到 2-selenoxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 10、11 和 13。 在 Biginelli 反应中使用乙酰丙酮作为底物产生了意想不到的 5-苯亚甲基-4,6-二甲基-嘧啶-2(5H)-硒酮 (14)。合成化合物的结构是在元素分析、红外、1H-和13C-NMR 和质谱数据的基础上确定的。图形概要
更新日期:2019-11-23
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