1,3-Dipolar Cycloadditions. Part XXXI. Selective Cycloadditions of C-(4-chlorophenyl)-N-phenyl Nitrone to Cinnamic Acid Anilides

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作者
Banerji, Avijit [1 ,5 ]
Sengupta, Sumana [1 ,2 ]
Prange, Thierry [3 ]
Neuman, Alain [4 ]
机构
[1] Univ Coll Sci & Technol, Ctr Adv Studies Nat Prod Including Synth, Dept Chem, Kolkata, W Bengal, India
[2] Chandernagore Coll, Dept Chem, Hooghly, W Bengal, India
[3] Fac Pharm, Lab Cristallog & RMN Biol, 4 Ave Observ, Paris, France
[4] Univ Paris 13, UFR SMBH, 74 Rue Marcel Cachin, F-93000 Bobigny, France
[5] Natl Res Inst Ayurved Drug Dev, 4-CN Block,Sect V, Kolkata, W Bengal, India
关键词
N-Cinnamoyl anilides; 1,3-Dipolar cycloaddition; Isoxazolidine; Nuclear magnetic resonance; X-ray powder diffraction; X-RAY; NMR; DFT;
D O I
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Investigations of the cycloaddition of C-(4-chlorophenyl)-N-phenyl nitrone to substituted cinnamic acid anilides were carried out. The predominant product in each reaction was the 3,4-trans-4,5-trans-4-carboxanilido-2,3,5-triaryl isoxazolidine cycloadduct, with much smaller amounts of the diastereoisomeric 3,4-cis-4,5-trans-4-carboxanilido-2,3,5-triaryl isoxazolidine cycloadduct. The products were characterized by detailed nuclear magnetic resonance studies and for selected compounds by X-ray diffraction analysis. [GRAPHICS] .
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页码:65 / 72
页数:8
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