Nucleophilic sulfanylation of 1,5-disubstituted pent-2-en-4-yn-1-ones

被引：20
|
作者：
Golovanov, A. A. [1 ]
Gusev, D. M. [1 ]
Vologzhanina, A. V. [2 ]
Bekin, V. V. [1 ]
Pisareva, V. S. [1 ]
机构：
[1] Togliatti State Univ, Tolyatti 445667, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 50卷 / 01期
关键词：
MICHAEL ADDITION; THIOLS; KETONES;
D O I：
10.1134/S1070428014010035
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselectivity of nucleophilic addition of benzenethiols and phenylmethanethiol to 1,5-diarylpent-2-en-4-yn-1-ones in ethanol in the presence of triethylamine at 0-30A degrees C is determined by the nucleophile nature. Phenylmethanethiol adds to the double bond, whereas benzenethiols add to the triple bond. The addition products, 1,5-diaryl-3-benzylsulfanylpent-4-yn-1-ones and 1,5-diaryl-5-(4-arylsulfanyl)penta-2,4-dien-1-ones, respectively, were isolated in 43-89% yield. Substituents in the aryl rings of the substrates did not affect the reaction direction.
引用
收藏
页码：13 / 20
页数：8
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