- Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: Efficient synthesis of 1,4,5-trisubstituted imidazoles
-
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
- Cai, Jinxiong,Bai, Haijie,Wang, Yuan,Xu, Xianxiu,Xie, Haiming,Liu, Jun
-
supporting information
p. 3821 - 3824
(2019/04/01)
-
- Rh-Catalyzed annulations of: N -methoxybenzamides with ketenimines: Synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties
-
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.
- Zhou, Xiaorong,Peng, Zhixing,Zhao, Hongyang,Zhang, Zhiyin,Lu, Ping,Wang, Yanguang
-
supporting information
p. 10676 - 10679
(2016/09/02)
-
- Preparation of 1,2,5-Trisubstituted 1H-Imidazoles from Ketenimines and Propargylic Amines by Silver-Catalyzed or Iodine-Promoted Electrophilic Cyclization Reaction of Alkynes
-
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.
- Zhou, Xiaorong,Jiang, Zheng,Xue, Lexing,Lu, Ping,Wang, Yanguang
-
p. 5789 - 5797
(2015/09/15)
-
- A convenient synthesis of ketenimines from thioamides with haloiminium salts
-
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.
- Shimizu, Masao,Gama, Yasuo,Takagi, Toshiyuki,Shibakami, Motonari,Shibuya, Isao
-
p. 517 - 520
(2007/10/03)
-
- Ketenimine Chemistry. Part 1. The Reaction of Triaryl Ketenimines with Arenesulphenyl Chlorides
-
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.
- Flowers, William T.,Halls, Audrey L.
-
p. 1255 - 1256
(2007/10/02)
-
- 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
-
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'-
- Dondoni, Alessandro,Battaglia, Arturo,Giorgianni, Patrizia
-
p. 3766 - 3773
(2007/10/02)
-