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Highly stereoselective synthesis of (Z)-3-methoxy-1-methyleneisoindoles via DMAP catalyzed cyclization of methyl 2-alkynylbenzimidates
Authors:Tuanli Yao  Xiujuan Liang  Zhen Guo  Dong Yang
Institution:1. College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi''an, 710021, China;2. Shaaxi Key Laboratory of Chemical Additives for Industry, Shaanxi University of Science and Technology, Xi''an, 710021, China
Abstract:A DMAP (4-dimethylaminopyridine) catalyzed cyclization of methyl 2-alkynylbenzimidates has been developed, which affords 3-methoxy-1-methyleneisoindoles with excellent Z-stereoselectivity under mild and transition-metal-free conditions. The (Z)-3-methoxy-1-methyleneisoindole products can be converted to corresponding 3-amino-1-methyleneisoindoles, 3-methoxy-isoindoles, 3-methyleneisoindolinones and isoindolinones with high efficiency.
Keywords:Corresponding author  College of Chemistry and Chemical Engineering  Shaanxi University of Science and Technology  Xi'an  710021  China    Cyclization  Metal-free  2-Alkynylbenzimidates  3-Methoxy-1-methyleneisoindoles
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