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Synfacts 2011(9): 0937-0937
DOI: 10.1055/s-0030-1260989
DOI: 10.1055/s-0030-1260989
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Arynes in the Synthesis of N-Arylisatins
D. C. Rogress, R. C. Larock*
Iowa State University, Ames, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
19. August 2011 (online)
![](https://www.thieme-connect.de/media/synfacts/201109/lookinside/thumbnails/10.1055-s-0030-1260989-1.jpg)
Significance
Reported is an efficient synthesis of isatins from the reaction of in situ generated arynes with methyl 2-oxo-2-(arylamino)acetates by simply stirring the reagents overnight in MeCN with a large excess of CsF. The yields range from mediocre to good, and the scope was well studied. The yields are slightly lower with electron-poor aryne substrates compared to electron-rich substrates. The reaction fails utterly for nitro-substituted substrates, which is attributed to a reaction of the aryne with the nitro group, behavior observed by the authors also previously (D. C. Rogness, R. C. Larock Tetrahedron Lett. 2009, 50, 4003).