Tetrahedron Letters

Formation of N-substituted 4-and 7-oxo-4, 5, 6, 7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4-and 7-oxoindoles

AG Montalban, SM Baum, J Cowell, A McKillop

Index: Montalban, Antonio Garrido; Baum, Sven M.; Cowell, Justin; McKillop, Alexander Tetrahedron Letters, 2012 , vol. 53, # 33 p. 4276 - 4279

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Citation Number: 6

Abstract

An efficient method for the preparation of 4-oxo-4, 5, 6, 7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4, 5, 6, 7-tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4-and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4-and 7-oxo-4, 5, 6, 7-tetrahydroindole ...