- α-Oxo-Ketenimines from Isocyanides and α-Haloketones: Synthesis and Divergent Reactivity
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The palladium-catalyzed reaction of α-haloketones with isocyanides afforded α-oxo-ketenimines through β-hydride elimination of the β-oxo-imidoyl palladium intermediates. Reaction of these relatively stable α-oxo-ketenimines with nucleophiles such as hydrazines, hydrazoic acid, amines, and Grignard reagent afforded pyrazoles, tetrazole, β-keto amidines, and enaminone, respectively, with high chemoselectivity. Whereas amines attack exclusively on the ketenimine functions, the formal [3+2] cycloaddition between N-monosubstituted hydrazines and α-oxo-ketenimines was initiated by nucleophilic addition to the carbonyl group.
- Mamboury, Mathias,Wang, Qian,Zhu, Jieping
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supporting information
p. 12744 - 12748
(2017/09/25)
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- α-Cycloalkyl-substituted ω-keto-dicarboxylic acids as lipid regulating agents
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A series of cycloalkyl-substituted oxo-alkanedicarboxylic acids have been prepared by the TosMIC methodology departing from haloalkyl-substituted cycloalkylcarboxylic esters. cyclopropyl derivatives showed IC50 activity in the 0.3-1.0 μM range
- Bell, Roel P.L.,Verdijk, Dennis,Relou, Mike,Smith, Dennis,Regeling, Henk,Ebbers, Eelco J.,C. Leemhuis, Frank M.,Oniciu, Daniela C.,Cramer, Clay T.,Goetz, Brian,Pape, Michael E.,Krause, Brian R.,Dasseux, Jean-Louis
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p. 223 - 236
(2007/10/03)
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- A SYNTHETHIC ROAD TO THE FOREST OF STRYCHNOS, ASPIDOSPERMA, SCHIZOZYGANE AND EBURNAMINE ALKALOIDS BY WAY OF THE NOVEL PHOTOISOMERIZATION
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The novel photoisomerization of 1-acylindoles accompanied by a conversion of indole to indolenine afforded 3-acylindolenines, a so far unknown reactive species, as a major product.This reaction was thorougly investigated and applied with success to the total synthesis of Strychnos, Aspidosperma, Schizozygane and Eburnamine alkaloids through a versatile intermediate 9-membered ring system,synthesized in a one pot reaction by photolysis and the simultaneous ring enlargement.
- Ban, Yoshio,Yoshida, Kiyoshi,Goto, Jiro,Oishi, Takeshi,Takeda, Eiko,Ishigamori
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p. 3657 - 3668
(2007/10/02)
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