Geminally activated β-nitrostyrenes in reactions with cyclic β-diketones

被引:8
作者
Berestovitskaya, V. M. [1 ]
Baichurin, R. I. [1 ]
Baichurina, L. V. [1 ]
Fel'gendler, A. V. [1 ]
Aboskalova, N. I. [1 ]
机构
[1] Herzen State Pedag Univ Russia, St Petersburg 191186, Russia
关键词
DIASTEREOSELECTIVE SYNTHESIS; ALPHA-NITROACRYLATES; DERIVATIVES; 2,3-DIHYDROFURANS;
D O I
10.1134/S1070363213090211
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The interaction of gem-benzoylnitroethenes and gem-alkoxycarbonylnitroethenes with cyclic beta-diketones (dihydroresorcinol and dimedone) occurs as a one-pot process via sequential Ad(N) and S-N steps followed by denitration to give functionally substituted hexahydrobenzofurans. The intermediate products of the nucleophilic addition have been isolated in the reactions of gem-acetylnitroethenes with dihydroresorcinol. The structures of the synthesized compounds have been confirmed by IR, H-1, and C-13-{H-1} spectroscopy including the heteronuclear correlation experiments (H-1-C-13 HMQC and H-1-C-13 HMBC).
引用
收藏
页码:1755 / 1763
页数:9
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