金催化肌酸酐与靛红的加成反应:一种可持续的绿色方法用于非对映选择合成3-取代的3-羟基靛红

doi:10.1016/S1872-2067(17)62812-2

催化学报 ›› 2017, Vol. 38 ›› Issue (5): 775-783.DOI: 10.1016/S1872-2067(17)62812-2

金催化肌酸酐与靛红的加成反应:一种可持续的绿色方法用于非对映选择合成3-取代的3-羟基靛红

K. Parthasarathy^a, T. Ponpandian^b, C. Praveen^c

a. 悉达中央研究委员会悉达中央研究所化学系, Arumbakkam, 金奈 600106, 泰米尔纳德邦, 印度;
b. 工业发展区私人有限实验室, 海得拉巴 500076, 特伦甘纳邦, 印度;
c. 中央电化学研究所功能材料部科学和工业研究理事会, 卡拉库迪 600006, 泰米尔纳德邦, 印度

收稿日期:2017-01-05 修回日期:2017-02-28 出版日期:2017-05-18 发布日期:2017-05-10
通讯作者: C. Praveen

Gold-catalyzed addition reaction between creatinine and isatin: A sustainable and green chemistry approach for the diastereoselective synthesis of 3-substituted-3-hydroxyisatins

K. Parthasarathy^a, T. Ponpandian^b, C. Praveen^c

a. Department of Chemistry, Siddha Central Research Institute, Central Council for Research in Siddha (CCRS), Arumbakkam, Chennai-600106, Tamil Nadu, India;
b. Inogent Laboratories Private Limited, Industrial Development Area Nacharam, Hyderabad-500076, Telangana, India;
c. Functional Materials Division, Council of Scientific and Industrial Research-Central Electrochemical Research Institute (CSIR-CECRI), Karaikudi-600006, Tamil Nadu, India

Received:2017-01-05 Revised:2017-02-28 Online:2017-05-18 Published:2017-05-10

摘要/Abstract

摘要：

报道了水介质中金催化肌酸酐与不同靛红之间的醛醇缩合反应.该法无需繁杂的溶剂萃取和柱色谱技术，只需简单的过滤即可将产物分离出来，因而操作简单.通过较宽范围的靛红衍生物的反应，均可高产率并完全地制取相应的顺式醛醇缩合产物，因此该法表现出较高的通用性.还将该合成策略进一步拓展至靛红，肌酸酐和丙二腈的串联反应，可高产率、完全的制取反式多组分产物.采用分光光度法测定了合成产物的抗氧化性能，结果表明，与标准物相比，含有卤素原子的三个化合物（2c，2d和2e）表现出最高的活性.

关键词: 肌酸酐, 金催化, 绿色化学, 非对映立体选择性, 抗氧化剂

Abstract:

The aldolization of various isatins with creatinine under gold catalysis in water has been developed. The reaction is operationally simple as the products can be isolated by simple filtration without requiring tedious solvent extraction and column chromatographic techniques. The generality of this methodology is showcased through the reactions of a wide range of isatin derivatives with creatinine to afford the respective aldol products in excellent yields with complete syn-selectivity. The scope of this chemistry is further extended to a tandem reaction involving isatins, creatinine and malononitrile to afford multicomponent products in excellent yields with complete anti-selectivity. The antioxidant potency of the synthesized compound was assessed by a spectrophotometric method, which revealed that three compounds containing halogen atoms (2c, 2d and 2e) were the most active compared with the standard.

Key words: Creatinine, Gold catalysis, Green chemistry, Diastereoselectivity, Antioxidant

K. Parthasarathy, T. Ponpandian, C. Praveen. 金催化肌酸酐与靛红的加成反应:一种可持续的绿色方法用于非对映选择合成3-取代的3-羟基靛红[J]. 催化学报, 2017, 38(5): 775-783.

K. Parthasarathy, T. Ponpandian, C. Praveen. Gold-catalyzed addition reaction between creatinine and isatin: A sustainable and green chemistry approach for the diastereoselective synthesis of 3-substituted-3-hydroxyisatins[J]. Chinese Journal of Catalysis, 2017, 38(5): 775-783.

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金催化肌酸酐与靛红的加成反应:一种可持续的绿色方法用于非对映选择合成3-取代的3-羟基靛红

Gold-catalyzed addition reaction between creatinine and isatin: A sustainable and green chemistry approach for the diastereoselective synthesis of 3-substituted-3-hydroxyisatins

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