American Chemical Society
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Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation

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journal contribution
posted on 2008-02-06, 00:00 authored by Christopher D. Gilmore, Kevin M. Allan, Brian M. Stoltz
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 total synthesis of the opiate alkaloid papaverine.