The oxidation of 3-heteroarylindoles to the corresponding oxindoles with t-butyl hypochlorite has been investigated. Under carefully adjusted conditions, preparative scale of desired products can be achieved. Two competing pathways seem to contribute to the reaction mechanism, affording 3-heteroaryloxindoles bearing hydrogen or chlorine at C3, depending on stereoelectronic factors. The present methodology appears also generally applicable for the preparation of simple 3-aryloxindoles.
Synthesis of 3-Heteroaryloxindoles through t-BuOCl-Mediated Oxidation of 3-Heteroarylindoles / M. Baroni, G. Lesma, L. Puleio, A. Sacchetti, A. Silvani, M. Zanchet. - In: SYNTHESIS. - ISSN 0039-7881. - :23(2010 Dec), pp. P12010SS.4075-P12010SS.4081. [10.1055/s-0030-1258289]
Synthesis of 3-Heteroaryloxindoles through t-BuOCl-Mediated Oxidation of 3-Heteroarylindoles
G. LesmaSecondo
;A. SilvaniPenultimo
;
2010
Abstract
The oxidation of 3-heteroarylindoles to the corresponding oxindoles with t-butyl hypochlorite has been investigated. Under carefully adjusted conditions, preparative scale of desired products can be achieved. Two competing pathways seem to contribute to the reaction mechanism, affording 3-heteroaryloxindoles bearing hydrogen or chlorine at C3, depending on stereoelectronic factors. The present methodology appears also generally applicable for the preparation of simple 3-aryloxindoles.
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