Orthogonal synthesis of indolines and isoquinolines via aryne annulation

CD Gilmore, KM Allan, BM Stoltz

Index: Gilmore, Christopher D.; Allan, Kevin M.; Stoltz, Brian M. Journal of the American Chemical Society, 2008 , vol. 130, # 5 p. 1558 - 1559

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Citation Number: 144

Abstract

Described in this report is the development of two unique methodologies exploiting the reactivity of arynes. Reaction of N-carbamoyl-functionalized enamine derivatives with benzyne affords substituted indolines. An orthogonal reactivity is uncovered when related enamine derivatives are modified as amides, such that isoquinolines are formed as the product of condensation with benzyne. This latter transformation is applied to a concise ...