5110-45-2Relevant academic research and scientific papers
Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: Efficient synthesis of 1,4,5-trisubstituted imidazoles
Cai, Jinxiong,Bai, Haijie,Wang, Yuan,Xu, Xianxiu,Xie, Haiming,Liu, Jun
supporting information, p. 3821 - 3824 (2019/04/01)
A novel base-mediated regioselective [3+2] annulation of active methylene isocyanides with ketenimines has been developed. In the presence of t-BuOK, a wide range of ketenimines readily react with active methylene isocyanides in DMF at 40 °C to afford 1,4
Rh-Catalyzed annulations of: N -methoxybenzamides with ketenimines: Synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties
Zhou, Xiaorong,Peng, Zhixing,Zhao, Hongyang,Zhang, Zhiyin,Lu, Ping,Wang, Yanguang
supporting information, p. 10676 - 10679 (2016/09/02)
Rhodium-catalyzed C-H activation/annulation reactions of ketenimines with N-methoxybenzamides furnished 3-aminoisoindolin-1-ones and 3-(diarylmethylene)isoindolin-1-ones. The synthesized 3-(diarylmethylene)isoindolin-1-ones exhibited aggregation induced emissions in aqueous tetrahydrofuran solution and strong green-yellow emissions in solids.
Preparation of 1,2,5-Trisubstituted 1H-Imidazoles from Ketenimines and Propargylic Amines by Silver-Catalyzed or Iodine-Promoted Electrophilic Cyclization Reaction of Alkynes
Zhou, Xiaorong,Jiang, Zheng,Xue, Lexing,Lu, Ping,Wang, Yanguang
, p. 5789 - 5797 (2015/09/15)
From readily available propargylic amines, 1,2,5-trisubstituted imidazoles are efficiently obtained through a cascade reaction catalyzed by AgOTf or promoted by molecular iodine. The AgOTf-catalyzed reaction involves nucleophilic addition of propargylic amine to ketenimine, a silver-catalyzed electrophilic cyclization reaction of alkyne, and a tautomerism/isomerism/metal-H exchange cascade. The iodine-mediated counterpart yields 5-formyl-1,2-disubtituted imidazoles, which presumably includes a cascade hydrolysis/oxidation reaction. Furthermore, the presented protocol can be scaled up and the resultant 1,2,5-trisubstituted imidazole can be converted into fused indeno[1,2-d]imidazole. 1,2,5-Trisubstituted imidazoles are efficiently prepared from readily available propargylic amines through a AgOTf-catalyzed or molecular iodine-promoted cascade reaction. The presented protocol can be scaled up and the resultant 1,2,5-trisubstituted imidazoles can be converted into fused indeno[1,2-d]imidazoles.
A convenient synthesis of ketenimines from thioamides with haloiminium salts
Shimizu, Masao,Gama, Yasuo,Takagi, Toshiyuki,Shibakami, Motonari,Shibuya, Isao
, p. 517 - 520 (2007/10/03)
Ketenimines were conveniently synthesized from N-monosubstituted thioacetamides with dehydrating agents such as 2-chloro-1,3- dimethylimidazolinium chloride or 2-chloro-1-methylpyridinium iodide.
Ketenimine Chemistry. Part 1. The Reaction of Triaryl Ketenimines with Arenesulphenyl Chlorides
Flowers, William T.,Halls, Audrey L.
, p. 1255 - 1256 (2007/10/02)
Benzenesulphenyl chloride reacts with diphenyl-N-p-tolylketenimine in diethyl ether solution to give N-(1-chloro-2,2-diphenyl-2-phenylthioethylidene)-p-toluidine (IV), via the attack of electrophilic sulphur on the terminal carbon of the ketenimine.
Selectivity in Ketenimine-Thioketone Cycloadditions. 1. 1,4- and 1,2-Addition Pathways and the Synthesis of 4H-3,1-Benzothiazines, 2-Iminothietanes, and Thioacrylamides
Dondoni, Alessandro,Battaglia, Arturo,Giorgianni, Patrizia
, p. 3766 - 3773 (2007/10/02)
The cycloadditions of thiobenzophenones to ketenimines take place at different sites of the cumulene depending on the extent of substitution and the nature of the substituents.C,C-Disubstituted ketenimines whose nitrogen bears an alkyl or an ortho,ortho'-
