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1,3-Bis(trifluoromethyl)prop-2-ene 1-Iminium Salts: Reactions with Alkoxybenzenes and Anilines
Synthesis ( IF 2.2 ) Pub Date : 2021-10-28 , DOI: 10.1055/a-1681-4823
Michael Keim 1 , Medina Jasarevic 2 , Ines Miller 2 , Gerhard Maas 2
Affiliation  

1,3-Bis(trifluoromethyl)prop-2-ene 1-iminium triflate salts were prepared for the first time and some synthetic applications as 1,3-biselectrophilic building blocks were established. They were found to react with dimethoxybenzenes or methylene-1,2-dioxybenzenes to furnish vinylogous trifluoroacetylation products (4-aryl-1,1,1,5,5,5-hexafluoropent-3-en-2-ones) and 1-dialkylamino-1,3-bis(trifluoromethyl)-1H-indenes. With aniline and ring-substituted anilines, 2,4-bis(trifluoromethyl)quinolines were formed. An unusual 4H-pyran, formally a condensation product of the N,N-dimethyl-1,3-bis(trifluoromethyl)prop-2-en-1-iminium ion and its enaminone precursor, is also reported.

中文翻译:

1,3-双(三氟甲基)丙-2-烯1-亚胺盐:与烷氧基苯和苯胺的反应

首次制备了 1,3-双(三氟甲基)丙-2-烯 1-亚胺三氟甲磺酸盐,并建立了一些作为 1,3-双亲电结构单元的合成应用。发现它们与二甲氧基苯或亚甲基-1,2-二氧基苯反应以提供乙烯基三氟乙酰化产物(4-芳基-1,1,1,5,5,5-六氟戊-3-en-2-ones)和1-二烷基氨基-1,3-双(三氟甲基)-1H-茚。与苯胺和环取代的苯胺一起形成 2,4-双(三氟甲基)喹啉。还报道了一种不寻常的 4H-吡喃,形式上是 N,N-二甲基-1,3-双(三氟甲基)prop-2-en-1-iminium 离子及其烯胺酮前体的缩合产物。
更新日期:2021-12-17
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