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

作者：Sun Jing; Gong Hui; Yan Chao Guo^*

来源：Tetrahedron, 2013, 69(48): 10235-10244.

DOI：10.1016/j.tet.2013.10.044

• Diels-Alder reaction
• Spirooxindole
• 1,2-Dihydropyridine
• [1,3]Oxazine
• Diastereoselectivity

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'-[2H,9aH-pyrido[2,1-b][1,3]oxazines], which were obtained from three-component reactions of pyridine and isatins with acetylenedicarboxylate or propiolate. H-1 NMR data and single crystal structures indicated that this reaction has both high regioselectivity and diastereoselectivity.

• 出版日期2013-12-2
• 单位扬州大学