Cu-II/TEMPO-Promoted One-Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters

Zhou Nini; Xie Tao; Li Zhongle; Xie Zhixiang

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Cu-II/TEMPO-Promoted One-Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters

机译：Cu-II / TEMPO促进的氨基酸酯高取代度嘧啶一锅合成

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A novel, Cu(OAc)(2)/TEMPO promoted one-step approach for the preparation of fully substituted pyrimidines from readily available amino acid esters has been described. In this reaction, the amino acid esters act as the only N-C sources for the construction of corresponding pyrimidines. The mechanism of this process includes oxidative dehydrogenation, the generation of an imine radical, and a formal [3+3] cycloaddition. This methodology proves to be a high atom-economic and straightforward strategy for the synthesis of pyrimidines and diverse substrates which are substituted by various functional groups have been afforded in moderate to good yield.

机译：已经描述了一种新型的Cu（OAc）（2）/ TEMPO促进的一步法，该方法用于从容易获得的氨基酸酯中制备完全取代的嘧啶。在该反应中，氨基酸酯充当构建相应嘧啶的唯一N-C源。该过程的机理包括氧化脱氢，亚胺基的产生和正式的[3 + 3]环加成。该方法被证明是用于合成嘧啶的高原子经济性和直接的策略，并且已经以中等至良好的产率提供了被各种官能团取代的各种底物。

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《Chemistry: A European journal》 |2014年第52期|共4页
作者
Zhou Nini; Xie Tao; Li Zhongle; Xie Zhixiang;
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正文语种 eng
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关键词
amino acid esters; copper; pyrimidines; radical reactions; reaction mechanisms;

机译：氨基酸酯;铜;嘧啶;自由基反应;反应机理;

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专利

1. Cu-II/TEMPO-Promoted One-Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters [J] . Zhou Nini, Xie Tao, Li Zhongle, Chemistry: A European journal . 2014,第52期

机译：Cu-II / TEMPO促进的氨基酸酯高取代度嘧啶一锅合成
2. A novel annulation reaction of N-substituted-2-nitrosoanilines with esters of α-isocyano acids. A one-pot, two-step route to 2-benzimidazole-substituted esters of α-amino acids [J] . Robert Bujok, Piotr Cmoch, Zbigniew Wrobel Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2014,第23期

机译：N-取代的2-亚硝基苯胺与α-异氰酸酯的新型环化反应。一锅二步制取2-苯并咪唑取代的α-氨基酸酯
3. CINCHONA ALKALOID THIOUREA-CATALYZED ONE-POT SYNTHESIS AND BIOSELECTIVE ACTIVITIES OF beta-AMINO ACID ESTER DERIVATIVES CONTAINING A PYRIMIDINE MOIETY [J] . Bai Song, Liu Shan, Zhu Yunying, Heterocycles: An International Journal for Reviews and Communications in Heterocyclic Chemistry . 2018,第8期

机译：Cinchona生物碱硫脲催化的含有嘧啶部分的β-氨基酸酯衍生物的一锅合成和生物选择性活性
4. Design, Synthesis, and Preferred Conformation of Peptides Based on a Highly Constrained, beta,beta'-Diphenyl Substituted Cyclopropane alpha-Amino Acid [C] . Soledad Royo, Wim M. De Borggraeve, Cristina Peggion American Peptide Symposium . 2006

机译：基于高约束的β-二苯基取代的环丙烷α-氨基酸的肽的设计，合成和优选构象
5. Synthesis of conformationally constrained glycosylated amino acids and synthesis of alpha-substituted serine amino acid analogs. [D] . Lane, Jonathan Webster. 2003

机译：构象约束的糖基化氨基酸的合成和α-取代的丝氨酸氨基酸类似物的合成。
6. Ultrasound Mediated One-Pot Three Component Synthesis Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-88a-dihydro-7H-(134)thiadiazolo(32-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents [O] . Shailee V. Tiwari, Julio A. Seijas, M. Pilar Vazquez-Tato, 2016

机译：超声介导的新型5-氨基-2-（4-氯苯基）-7取代苯基-88a-二氢-7H-（134）噻二唑的一锅三组分合成对接和ADME预测32-α）嘧啶-6-腈衍生物作为抗癌药
7. Ultrasound Mediated One-Pot, Three Component Synthesis, Docking and ADME Prediction of Novel 5-Amino-2-(4-chlorophenyl)-7-Substituted Phenyl-8,8a-dihydro-7H-(1,3,4)thiadiazolo(3,2-α)pyrimidine-6-carbonitrile Derivatives as Anticancer Agents [O] . Tiwari, Shailee V., Seijas, Julio A., Vázquez Tato, M. Pilar, 2016

机译：超声介导的新型5-氨基-2-（4-氯苯基）-7取代苯基-8,8a-二氢-7H-（1,3,4）噻二唑的一锅三组分合成，对接和ADME预测3,2-α）嘧啶-6-腈衍生物作为抗癌药

Cu-II/TEMPO-Promoted One-Pot Synthesis of Highly Substituted Pyrimidines from Amino Acid Esters

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