Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives

Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives
Ke Lu, Dong-Liang Mo, Chen-Xi Gu, Guo-Xue He, Gui-Fa Su, Cheng-Xue Pan, Feng Zhan, Xiang-Fei Kong
An efficient method to synthesize rutaecarpine derivatives via the gold-catalyzed selective cyclization of alkyn-tethered indoles under mild conditions is described. The alkyn-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation. Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp3 and sp2 hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02956

DOI: 10.1021/acs.joc.7b02956

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