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Synfacts 2009(6): 0605-0605  
DOI: 10.1055/s-0029-1216698
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Isoindolin-1-ones via Copper-Catalyzed Intramolecular Cyclization

Contributor(s): Victor Snieckus, Jignesh J. Patel
L. Li, M. Wang, X. Zhang, Y. Jiang*, D. Ma*
Shenyang Pharmaceutical University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

A CuI/l-proline-catalyzed synthesis of 3-methyleneisoindolin-1-ones is described by a sequential Sonogashira coupling of 2-bromobenz-amides with terminal alkynes followed by a carbo-amination (5-exo-dig cyclization) in one pot. In most cases only the Z-isomer product was observed. However, when nitro-substituted and N,N-diethylethylene-substituted aryl bromides were used, E-isomers were isolated as major products. A rationalization was not given.