Reaction of 5,5′-(1,4-Phenylene)bis(3-aryl-2-oxaspiro[5.5]undec-3-en-1-ones) with Methyl 1-Bromocyclohexanecarboxylate and Zinc

被引:0
|
作者
Nikiforova, E. A. [1 ]
Baibarodskikh, D. V. [1 ]
Shurov, S. N. [1 ]
Kusakina, E. V. [1 ]
Dmitriev, M. V. [1 ]
机构
[1] Perm State Natl Res Univ, Perm 614990, Russia
基金
俄罗斯基础研究基金会;
关键词
Reformatsky reaction; alicyclic Reformatsky reagents; methyl; 1-bromocyclohexanecmboxylate; alpha; beta-unsaturated carbonyl compounds; chalkones; dihydropyran-2-ones; spiranes; terephtaldehyde; X-ray diffraction;
D O I
10.1134/S1070428022020130
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 3,3'-(1,4-phenylene)bis(1-phenylprop-2-en-l-ones) with the Reformatsky reagent obtained from methyl 1-bromocyclohexanecarbovlate and zinc involves addition of two molecules of the reagent to the conjugated C=C-C=O systems of the substrate. The intermediate adducts undergo intramolecular cyclization via the nucleophilic attack of the enolate oxygen atoms on the carbonyl carbon atoms. The subsequent hydrolysis of the reaction mixture resulted in the isolation of bis(spiro-3,4-dihydropyran-2-ones). The structure of the products was confirmed by X-ray diffraction.
引用
收藏
页码:249 / 252
页数:4
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