Three-component access to pyrroles promoted by the CAN-silver nitrate system under high-speed vibration milling conditions: a generalization of the Hantzsch pyrrole synthesis.

Verónica Estévez, Mercedes Villacampa, J Carlos Menéndez

Index: Chem. Commun. (Camb.) 49(6) , 591-3, (2013)

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Abstract

A sequential multicomponent process involving the high-speed vibration milling of ketones with N-iodosuccinimide and p-toluenesulfonic acid, followed by addition of a mixture of primary amines, β-dicarbonyl compounds, cerium(IV) ammonium nitrate and silver nitrate afforded polysubstituted, functionalized pyrroles. This one-pot, solid-state process can be considered as the coupling of an α-iodoketone preparation with a general version of the classical Hantzsch pyrrole synthesis.