- Base-mediated regioselective [3+2] annulation of ketenimines and isocyanides: Efficient synthesis of 1,4,5-trisubstituted imidazoles
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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
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supporting information
p. 3821 - 3824
(2019/04/01)
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- Rh-Catalyzed annulations of: N -methoxybenzamides with ketenimines: Synthesis of 3-aminoisoindolinones and 3-diarylmethyleneisoindolinones with strong aggregation induced emission properties
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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
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supporting information
p. 10676 - 10679
(2016/09/02)
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- Preparation of 1,2,5-Trisubstituted 1H-Imidazoles from Ketenimines and Propargylic Amines by Silver-Catalyzed or Iodine-Promoted Electrophilic Cyclization Reaction of Alkynes
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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
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p. 5789 - 5797
(2015/09/15)
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- A convenient synthesis of ketenimines from thioamides with haloiminium salts
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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
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p. 517 - 520
(2007/10/03)
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- New synthesis of diphenyl-N-(substituted)ketenimines from diaminophosphonium diazaylides
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Diaminophosphonium diazaylides 2 react under mild conditions with diphenylacetyl chloride, to afford diphenyl-N-(substituted)ketenimines 4 or, depending on the case, their transformation products: either the tautomer 8, or the dimer 9. The general reactio
- Cristau, Henri-Jean,Jouanin, Isabelle,Taillefer, Marc
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- Titanium(III) Chloride Mediated Reduction of 1-Nitro-2-phenylethenes
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The reaction of 1-nitro-2-phenylethenes (β-nitrostyrenes) with aqueous titanium(III) chloride afforded substituted pyrroles in addition to the expected reduction products, oximes and carbonyl compounds. 2-Substituted 1-nitro-2-phenylethenes yielded divinylamine derivatives instead of pyrroles.The reaction mechanism has been rationalized by taking account of the electron transfer from titanium(III) species to the nitro olefines, followed by protonation, dimerization, cyclization, and/or hydrolysis.
- Sera, Akira,Fukumoto, Shoji,Tamura, Masako,Takabatake, Kiyoshi,Yamada, Hiroaki,Itoh, Kuniaki
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p. 1787 - 1791
(2007/10/02)
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