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Benzannulated Bicycles by Three-Component Aryne Reactions

Allan, Kevin M. and Gilmore, Christopher D. and Stoltz, Brian M. (2011) Benzannulated Bicycles by Three-Component Aryne Reactions. Angewandte Chemie International Edition, 50 (19). pp. 4488-4491. ISSN 1433-7851. https://resolver.caltech.edu/CaltechAUTHORS:20110606-080601724

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Abstract

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201100911DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201100911/abstractPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
Abbott UNSPECIFIED
AmgenUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
MerckUNSPECIFIED
Sigma-AldrichUNSPECIFIED
TevaUNSPECIFIED
CaltechUNSPECIFIED
NSFCHE-0639094
Subject Keywords:arynes; heterocycles; isocyanides; multicomponent reactions; polycycles
Issue or Number:19
Record Number:CaltechAUTHORS:20110606-080601724
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110606-080601724
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:23907
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:06 Jun 2011 15:40
Last Modified:03 Oct 2019 02:51

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