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Communication | Regular issue | Vol 92, No. 10, 2016, pp.1785-1795
Published online, 18th August, 2016
DOI: 10.3987/COM-16-13515
Oxidative Dearomatic Cyclization of N-Substituted Benzanilide Derivatives: Conformational Effect of Amide Groups on the Reaction

Kousuke Hayashi, Jun Takayama,* Meiyan Xuan, Misaki Suda, Hiroyuki Teramae, and Takeshi Sakamoto*

*Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan


The synthesis of spirooxindoles with a hypervalent iodine reagent depended on N-substituted benzanilide derivatives as starting materials. Reaction yields of benzanilides containing various N-substituents were discovered to relate to the cis and trans conformations of the amide bond by ab initio molecular orbital calculations at the B3LYP/6-31G(d,p) and MP2/6-31G(d,p) levels, including full geometry optimizations. The relationship between the reaction and conformation of the starting material by quantum chemical calculations was applied to the formal synthesis of SR121463.