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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
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
E-mail: josecm@farm.ucm.es
; Fax: +34 913941822
; Tel: +34 913941840
Chem. Commun., 2013,49, 591-593
DOI:
10.1039/C2CC38099D
Received
08 Nov 2012,
Accepted
26 Nov 2012
First published online
27 Nov 2012
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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