PhI (OCOCF3) 2-Mediated Cyclization of o-(1-Alkynyl) benzamides: Metal-Free Synthesis of 3-Hydroxy-2, 3-dihydroisoquinoline-1, 4-dione

…, X Zhang, D Zhang-Negrerie, Y Du…

Index: Zhang, Xiang; Zhang-Negrerie, Daisy; Deng, Jun; Du, Yunfei; Zhao, Kang Journal of Organic Chemistry, 2013 , vol. 78, # 24 p. 12750 - 12759

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Citation Number: 6

Abstract

The synthesis of an undocumented skeleton of 3-hydroxy-2, 3-dihydroisoquinoline-1, 4- diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl) benzamides in MeCN/H2O, mediated by metal-free, hypervalent reagent of PhI (OCOCF3) 2, followed by an oxidative hydroxylation reaction. The mechanism consisting of two pathways has been proposed and discussed.