One-pot Two-Step Cycloaddition Reaction for Convenient Synthesis of Polycyclic Spirooxindole-fused [1,3]Oxazines  

作　　者：Jing Sun Hui Gong Chaoguo Yan 

机构地区：[1]College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China

出　　处：《Chinese Journal of Chemistry》2015年第9期1049-1056,共8页中国化学（英文版）

基　　金：This work was financially supported by the National Natural Science Foundation of China （Grant No. 21272200） and the Priority Academic Program Development of Jiangsu Higher Education Institutions. We would also like to express our sincere thanks to the Analysis Center of Yangzhou University for providing all necessary instruments for characterization of structures.

摘　　要：The novel spirooxindoline fused [1,3]oxazines were efficiently synthesized from Diels-Alder reaction of N-arylmaleimides with 1,2-dihydro-2-oxospiro[3H-indole-3,2＇-[2H,9aH-pyrido[2,1-b][l,3]oxazines], which were generated in situ from three-component reactions of substituted pyridines and isatins with methyl propiolate, or di- methyl acetylenedicarboxylate. The stereochemistry of the products was clearly clarified by the analysis of 1H NMR data and single crystal structures of the obtained polycyclic compounds.The novel spirooxindoline fused [1,3]oxazines were efficiently synthesized from Diels-Alder reaction of N-arylmaleimides with 1,2-dihydro-2-oxospiro[3H-indole-3,2＇-[2H,9aH-pyrido[2,1-b][l,3]oxazines], which were generated in situ from three-component reactions of substituted pyridines and isatins with methyl propiolate, or di- methyl acetylenedicarboxylate. The stereochemistry of the products was clearly clarified by the analysis of 1H NMR data and single crystal structures of the obtained polycyclic compounds.

关 键 词：Diels-Alder reaction one-pot reaction DIASTEREOSELECTIVITY SPIROOXINDOLE [1 3]oxazine MALEIMIDE 

分 类 号：O626[理学—有机化学] O621.263[理学—化学]