Phosphine-catalyzed [3+2] cycloaddition of Morita—Baylis—Hillman carbonates to isothiocyanates in the synthesis of adamantane-containing trisubstituted aminothiophenes

被引:0
作者
I. S. Zenkov
A. S. Abel
A. D. Averin
G. M. Butov
I. P. Beletskaya
机构
[1] Lomonosov Moscow State University,Department of Chemistry
[2] Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences,undefined
[3] Volzhsky Polytechnic Institute (branch) of Volgograd State Technical University,undefined
来源
Russian Chemical Bulletin | 2021年 / 70卷
关键词
thiophene; organocatalysts; phosphines; adamantane; isothiocyanates; Morita—Baylis—Hillman carbonates;
D O I
暂无
中图分类号
学科分类号
摘要
An addition of the Morita—Baylis—Hillman (MBH) carbonates to adamantane-containing isothiocyanates was studied. The MBH carbonates react with 1-(4-isothiocyanatophenyl)-adamantane in the presence of triphenylphosphine to give 5-aryl-substituted adamantane-containing 2-amino-4-methoxycarbonylthiophenes in 31–59% yields, while 1- and 2-isothio-cyanatoadamantanes were found unreactive in this reaction.
引用
收藏
页码:880 / 884
页数:4
相关论文
共 22 条
[21]   Synthesis of novel and diverse naphtho[1,2-b]furans by phosphine-catalyzed [3+2] annulation of activated 1,4-naphthoquinones and acetylenecarboxylates [J].
Xia, Likai ;
Magar, Krishna Bahadur Somai ;
Lee, Yong Rok .
MOLECULAR DIVERSITY, 2015, 19 (01) :55-66
[22]   Highly Z-Selective Synthesis of Highly Substituted 1,3-Oxathiolane-2-imines via TfOH-Catalyzed Formal [3+2] Cycloaddition of Donor-Acceptor Oxiranes and Isothiocyanates [J].
Zhan, Feng ;
Wang, Zhe ;
Wu, Guan-Zheng ;
Shi, Zhichao ;
Zhang, Xun ;
Zuo, Qinglu ;
Lin, Jin-Shun ;
Jiang, Yuyang .
CHEMISTRYSELECT, 2021, 6 (13) :3151-3154