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Synfacts 2009(5): 0490-0490  
DOI: 10.1055/s-0029-1216608
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3,4-Dihydro-2(¹H)-quinolinone via Ring Expansion

Contributor(s): Victor Snieckus, Josefine Karlsson
T. Tsuritani*, Y. Yamamoto, M. Kawasaki, T. Mase
Banyu Pharmaceutical Co. Ltd., Tsubaki, Japan
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Publikationsdatum:
22. April 2009 (online)

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Significance

Described is a synthetic method for the construction of 3,4-dihydro-2(¹H)-quinolin­ones via palladium-catalyzed cyclopropane ring expansion from N-(1′-alkoxy)cyclopropyl-2-halo­anilines. The method is also applicable to the synthesis of 5,6-dihydrobenzimidazol[1,2-a]quinoline. N-(1′-alkoxy)cyclopropyl-2-haloanilines were readily prepared according to Yoshida’s procedure with (1-ethoxycyclopropoxy)-trimethylsilane from the corresponding 2-haloanilines (Y. Yoshida et al. Synlett 2003, 2139).