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Synfacts 2009(6): 0603-0603
DOI: 10.1055/s-0029-1216703
DOI: 10.1055/s-0029-1216703
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Platinum-Catalyzed Cascade Synthesis of Indoloquinazolinones
I. Nakamura*, Y. Sato, M. Terada
Tohoku University, Sendai, Japan
Further Information
Publication History
Publication Date:
25 May 2009 (online)
![](https://www.thieme-connect.de/media/synfacts/200906/lookinside/thumbnails/10.1055-s-0029-1216703-1.jpg)
Significance
Reported is a one-pot platinum(IV) iodide dihydroxylation-cyclization synthesis of indoloquinazolinones. A plausible mechanism is proposed and is consistent with the rational for performing the cascade. The first step is the coordination of platinum to the alkyne for activating it towards the nucleophilic attack by the N-alkoxyamide to form the six-membered ring. Formation of a platinum carbenoid facilitates the ejection of hydroxide to give an iminium species. Insertion of the ortho C-H bond into the platinum carbenoid generates the five-membered ring, which after a proton transfer yields the final product.