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Synfacts 2010(3): 0283-0283
DOI: 10.1055/s-0029-1219428
DOI: 10.1055/s-0029-1219428
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Platinum-Catalyzed Synthesis of Indoles and Isoquinolines from 2-Alkynylarylamides
N. Okamoto, Y. Miwa, H. Minami, K. Takeda, R. Yanada*
Hiroshima International University, Japan
Further Information
Publication History
Publication Date:
18 February 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201003/lookinside/thumbnails/10.1055-s-0029-1219428-1.jpg)
Significance
In continuation of the In(OTf)3-catalyzed synthesis of 1,2-dihydroisoquinolines from 2-alkynylarylaldimines (R. Yanada, S. Obika, H. Kono, Y. Takemoto Angew. Chem. Int. Ed. 2006, 45, 3822), the platinum(II)-catalyzed synthesis of indoles and isoquinolines from isocyanates 2 is reported. After a Hofmann rearrangement of amides 1 using (diacetoxyiodo)benzene, the resulting isocyanates 2 undergo an intramolecular cyclization into an activated alkyne under PtCl2 catalysis to give products 3. This methodology was applied to the synthesis of macrocyclic bis(indole) 4 via macrocycle bis(ynecarbamate) 5. Structures 3 and 4 were secured by X-ray crystallographic analysis.