Diastereoselective synthesis of dispirooxindoline fused [1,3]oxazines via Diels-Alder reaction of functionalized 1,2-dihydropyridines with (E)-1,3-dihydro-3-phenacylidene-2H-indol-2-ones

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• 作者：Jing Sun ; Hui Gong ; Chao-Guo Yan
• 关键词：Diels&ndash ; Alder reaction ; Spirooxindole ; 1 ; 2-Dihydropyridine ; [1 ; 3]Oxazine ; Diastereoselectivity
• 刊名：Tetrahedron
• 出版年：2 December, 2013
• 年：2013
• 卷：69
• 期：48
• 页码：10235-10244
• 全文大小：778 K

文摘

An efficient synthetic procedure for the complex dispirooxindoline fused [1,3]oxazines was successfully developed via Diels-Alder reaction of (E)-1,3-dihydro-3-phenacylidene-2H-indol-2-ones with 1,2-dihydro-2-oxospiro[3H-indole-3,2鈥?[2H,9aH-pyrido[2,1-b][1,3]oxazines], which were obtained from three-component reactions of pyridine and isatins with acetylenedicarboxylate or propiolate. ¹H NMR data and single crystal structures indicated that this reaction has both high regioselectivity and diastereoselectivity.