Organic Chemistry Portal



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:

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

DOI: 10.1021/ja0780582 (free Supporting Information)

see article for more reactions


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.

see article for more examples

Key Words


ID: J48-Y2008-0300