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

作者：Yang, Chao; Zhang, Xiang; Zhang-Negrerie, Daisy; Du, Yunfei^*; Zhao, Kang

来源：Journal of Organic Chemistry, 2015, 80(10): 5320-5328.

DOI：10.1021/acs.joc.5b00576

• N BOND FORMATION
• MEDIATED ALKYNE AMIDATION
• INTRAMOLECULAR CYCLIZATION
• STEREOSELECTIVE-SYNTHESIS
• POLYVALENT IODINE
• ORGANIC-SYNTHESIS
• ELECTROPHILIC CYCLIZATION
• OXIDATIVE CYCLIZATION
• CONVENIENT SYNTHESIS
• EFFICIENT SYNTHESIS

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:

• 出版日期2015-5-15
• 单位天津大学