Intermolecular nitroso Diels-Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium

被引:29
|
作者
Calvet, G [1 ]
Guillot, R [1 ]
Blanchard, N [1 ]
Kouklovsky, C [1 ]
机构
[1] Inst Chim Mol & Mat Orsay, UMR CNRS 8615, Lab Synth Subst Nat, F-91400 Orsay, France
关键词
D O I
10.1039/b513397a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Diels-Alder cycloadditions of the alpha-acetoxynitroso dienophile 1 in water are reported. The rapid and high yielding synthesis of structurally diverse 3,6-dihydro-1,2-oxazines complements the straightforward elaboration of aminoalcohols obtained from the alpha-acetoxynitroso derivative 1 in anhydrous medium. A rationale for this solvent-dependent product distribution is proposed.
引用
收藏
页码:4395 / 4401
页数:7
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