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.

Chem Commun (Camb)

Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain.

Published: January 2013

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.

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http://dx.doi.org/10.1039/c2cc38099dDOI Listing

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