Benzannulated Bicycles by Three-Component Aryne Reactions
Triple crown: A pair of three-component coupling reactions between arynes, isocyanides, and either activated alkynes or phenyl esters generates unusual iminoindenones or phenoxy iminoisobenzofurans (see scheme), the latter of which may be advanced to o-ketobenzamides by performing direct hydrolysis. The synthetic utility of these compounds is demonstrated in a rapid preparation of substituted dibenzoketocaprolactams.
Additional Information© 2011 Wiley-VCH Verlag. Received: February 5, 2011. Article first published online: 11 Apr 2011. The authors thank Abbott, Amgen, Boehringer Ingelheim, Bristol-Myers Squibb, Merck, Sigma–Aldrich, Teva, and Caltech for financial support. Lawrence Henling and Dr. Michael Day are gratefully acknowledged for X-ray crystallographic structural determination. The Bruker KAPPA APEX II X-ray diffractometer was purchased through an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094. Dr. Scott C. Virgil is acknowledged for helpful discussions.
Supplemental Material - anie_201100911_sm_miscellaneous_information.pdf