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Orthogonal Synthesis of Indolines and Isoquinolines via Aryne Annulation

Christopher D. Gilmore, Kevin M. Allan and Brian M. Stoltz*

*Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, Email: stoltzcaltech.edu

C. D. Gilmore, K. M. Allan, B. M. Stoltz, J. Am. Chem. Soc., 2008, 130, 1558-1559.

DOI: 10.1021/ja0780582 (free Supporting Information)


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Abstract

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.

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Key Words

Isoquinolines


ID: J48-Y2008-0300