A Practical Synthesis of Densely Functionalized Pyrroles via a Three-Component Cascade Reaction between Carbohydrates, Oxoacetonitriles, and Ammonium Acetate

• DOI: 10.1021/acs.joc.0c02381
• Publication Date: 2020-12-17T20:51:25Z
• Authors: Mengxin Xia; Mallikharjuna Rao...; Madhu Babu Tatina; Zaher M. A. Judeh
• Keywords: Atom economy; Cascade reaction; Reaction conditions

A practical three-component reaction between unactivated carbohydrates, oxoacetonitriles, and ammonium acetate gave densely functionalized pyrroles in 75–96% yields. Disaccharides afforded novel pyrrolo-glycosides. This metal-free, Et3N-catalyzed cascade proceeded with exclusive chemo-, regio-, stereoselectivities showed a wide substrate scope high atom economy. It also successfully at 2 g scale, demonstrating potential for large-scale synthesis. The functional groups on the permit easy transformation to other handles construction of more complex structures. through mechanism involving several intermediates identified by mass spectrometric analysis. work has great sustainable production from cheap widely available carbohydrates represents key advancement synthesis these ubiquitous heterocycles.