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Updated: Apr 23, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Copper(II)-catalyzed indolizines formation followed by dehydrogenative functionalization cascade to synthesize
Fuyao Wang1, Yongmiao Shen, Huayou Hu
1Jiangsu Key Laboratory of Green Synthetic for Functional Materials and School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, Jiangsu, P. R. China.
Abstract:
A one-pot, three-component cascade reaction between pyridine, α-acylmethylbromide, and maleic anhydride leading to direct access of 1-bromoindolizines in high yields has been developed. This protocol is accomplished via a reaction sequence of 1,3-dipolar cycloaddition of the pyridinium ylide with maleic anhydride, oxidative decarboxylation of the primary cycloadduct, and dehydrogenative bromination of the resulting 1-unsubstituted indolizine. Copper chloride was used as a catalyst and oxygen as the terminal oxidant. This reaction represents the first example of transition-metal-catalyzed direct dehydrogenative bromination of indolizine at the C-1 position. Moreover, the obtained 1-bromoindolizines can be transformed to other 1-substituted indolizines such as 1-arylindolizines via a simple reaction process.
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