Base-Promoted Three-Component Cascade Reaction of α-Hydroxy Ketones, Malonodinitrile, and Alcohols: Direct Access to Tetrasubstituted NH-Pyrroles

作者：Liu, Hongjian; Qi, Chaorong^*; Wang, Lu; Guo, Yanhui; Li, Dan; Jiang, Huanfeng^*

来源：Journal of Organic Chemistry, 2021, 86(14): 9610-9620.

DOI：10.1021/acs.joc.1c00882

• POLYSUBSTITUTED PYRROLES
• REGIOSELECTIVE SYNTHESIS
• DIVERGENT SYNTHESIS
• METAL-FREE
• ANNULATION
• CYCLIZATION
• DERIVATIVES
• REARRANGEMENT
• CYCLOADDITION
• DIKETONES

A base-promoted three-component cascade reaction of alpha-hydroxy ketones, malonodinitrile, and alcohols has been developed, providing a direct and efficient route to a range of structurally diverse and synthetically useful 2-alkyloxy-1H-pyrrole-3-carbonitrile derivatives. The reaction involved three different bond (C-C, C-O, and C-N) formations in a single step, and its regioselectivity was depended on the structure of the alpha-hydroxy ketones employed. The use of easily available starting materials, wide substrate scope, good functional group tolerance, operational simplicity, and high atom economy are attractive features of the new method.