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不对称合成新型的吲哚螺-2,3-二氢呋喃衍生物 被引量:1

Asymmetric synthesis of novel spirooxindol-2,3-dihydrofuran compounds
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摘要 在辛可宁的作用下,以靛红衍生物(N-甲基-3-羟基-2-吲哚酮)和氰基苯乙烯衍生物为原料,1,3,5-三甲苯为溶剂,合成了一系列的新型的手性吲哚螺-2,3-二氢化呋喃衍生物.该反应产率较高(90%~99%),选择性较好,而且操作简单、后处理方便.产物的结构经红外光谱、核磁共振谱(1H,13C)及高分辨质谱法表征. A series of novel spirooxindol-2,3-dihydrofuran compounds were synthesized by the reaction of isa- tin derivatives (3-hydroxy-l-methylindolin-2-one) and cinnamonitrile derivatives in mesitylene in the presence of cinchonine. The reaction had excellent yields, high enantioselectivity, simple operation and easy post-pro- cessing. The structures of the products were determined by IR, NMR ( 1 H, 13 C) and HRMS analysis.
出处 《浙江师范大学学报(自然科学版)》 CAS 2014年第1期84-92,共9页 Journal of Zhejiang Normal University:Natural Sciences
关键词 辛可宁 靛红 不对称合成 立体选择性 螺环 cinchonine isatin asymmetric synthesis enantioselectivity spirocyclic
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  • 1N akamura I, Chan C S, Araki T, et al. Synthesis of multisubstituted 2-( dihydrofuran-2 (3H)-yhdene)acetates via intramolecular carboalkoxyla- tion by platinum-olefin catalyst system[J]. Org Lett,2008,10(2) :309-312.
  • 2Li Mengru, Lin Shaoxia, Dong Zhiyong, et al. Organoeatalyzed anion elay leading to functionalized 2,3-dihydrofurans [ J ]. Org Lett, 2013,15 ( 15 ) :3978-3981.
  • 3Chen Guodong, Cao Weiguo, Chen Jie, et al. High stereoselective synthesis of trans-2,3-dihydrofuran derivatives [ J ]. Synth Comm, 2004,34 ( 20 ) : 3793-3799.
  • 4Sugimura H, Osumi K, Kodaka Y. Stereoselective synthesis of 2'-deoxy-D-threo-pentofuranosyl nucleosides by the NBS promoted coupling re- action of thioglycosides with silylated heterocyclic bases[ J]. J Org Chem, 1994,59 (25) :7655-7660.
  • 5Gianturco M A, Friedel P, Flanagan V. A novel procedure for the synthesis of 2,3-dihydrofurans [ J ]. Tetrahedron Lett, 1965,6 (23) : 1847- 1852.
  • 6魏荣宝,刘博,刘洋,郭金晶,张大为.具有生理活性的含氧、氮、硫杂原子螺环化合物的研究进展[J].有机化学,2008,28(9):1501-1514. 被引量:8
  • 7魏荣宝,刘洋,梁娅.含螺环结构农药研究进展[J].有机化学,2009,29(3):476-487. 被引量:14
  • 8Gianotti M, Andrehti D, Casotto D, et al. Asymmetric route to spirotetracyclic (1S) -5', 11 '-dihydro-3 H-spiro [ cyclopentane-1,10'-dibenzo [ a, d] cyclohepten]-3-one derivatives[J]. Tetrahedron Lett,2011,52(2) :329-331.
  • 9Chiba S,Zhang L, Lee J Y. Copper-catalyzed synthesis of azaspirocyclohexadienones from a-azido-N-arylamides under an oxygen atmosphere [J]. J Am Chem Soc,2010,132(21 ) :7266-7267.
  • 10Singh G S, Desta Z Y. Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks [ J ]. Chem Rev ,2012,112 ( 11 ) : 6104-6155.

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