One-pot construction of spirooxindole backbone via biocatalytic domino reaction. Issue 30 (26th July 2017)

• Record Type: Journal Article
• Authors: Liang, Yi-Ru; Hu, Yu-Jing; Zhou, Xue-Han; Wu, Qi; Lin, Xian-Fu
• Is Part Of: Tetrahedron letters. Volume 58:Issue 30(2017)
• Page Start: 2923
• Page End: 2926
• Publication Date: 2017-07-26
• Subjects: Spirooxindole -- Enzyme -- One-pot -- Fluorescent properties; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.06.031
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: We report a one-pot papain-catalyzed reaction to synthesize spiropyrazolo[3, 4- b ]pyridines in ethanol for the first time. 9 spiropyrazolo[3, 4- b ]pyridines are obtained in acceptable yields. We propose a tentative mechanism to explain the papain-catalyzed process. Most of the products show strong fluorescence emission ability, providing great potential application in the field of fluorescent material. Abstract: A simple and environmentally friendly method to synthesize spiropyrazolo[3, 4- b ]pyridines derivatives starting from isatin, cyclic-1, 3-diketone and 3-methyl-5-aminopyrazole was developed. With the optimized conditions for enzymes, solvents, enzyme loading and reaction time in hand, 9 compounds were obtained in acceptable yields. Moreover, the investigation in fluorescent properties of these products showed their potential application in the field of new fluorescent material.