- Copper-catalyzed β-trifluoromethylation of conjugated hydrazones
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The Cu-catalyzed direct β-trifluoromethylation of α,β-unsaturated aldehyde N,N-dibenzylhydrazones with Togni hypervalent iodine reagent is described. The reaction yields stereodefined CF3-alkenyl derivatives under mild conditions and is propose
- Prieto, Alexis,Jeamet, Emeric,Monteiro, Nuno,Bouyssi, Didier,Baudoin, Olivier
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- Gold(I)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: Efficient access to highly substituted cyclobutanes
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α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.
- Bernal-Albert, Paloma,Faustino, Hlio,Gimeno, Ana,Asensio, Gregorio,Mascarenas, Jos L.,Lpez, Fernando
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supporting information
p. 6196 - 6199
(2015/02/19)
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- Insertion of Nitriles into Zirconocene 1-aza-1,3-diene Complexes: Chemoselective Synthesis of N-H and N-Substituted Pyrroles
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The direct insertion of nitriles into zirconocene-1-aza-1,3-diene complexes provides an efficient, chemoselective, and controllable synthesis of N-H and N-substituted pyrroles upon acidic aqueous work-up. The outcome of the reaction (that is, the formatio
- Yu, Shasha,Xiong, Meijun,Xie, Xin,Liu, Yuanhong
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supporting information
p. 11596 - 11599
(2016/02/19)
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- One-pot tandem 1,4- and 1,2-addition of phosphites to α,β- unsaturated hydrazones
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The 1,4- and 1,2-addition of phosphites to α,β-unsaturated hydrazones was investigated. When silylated phosphites and trialkyl phosphites were compared, trialkyl phosphites gave better conversions and subsequently higher yields. A variety of hydrazones we
- Stevens, Christian V.,Van Meenen, Ellen,Masschelein, Kurt G. R.,Moonen, Kristof,De Blieck, Ann,Drabowicz, Jozef
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p. 2549 - 2552
(2008/02/13)
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- New phosphonate reagents for aldehyde homologation
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New phosphonate reagents were developed for the two-carbon homologation of aldehydes to unbranched or methyl-branched unsaturated aldehydes. The phosphonate reagents, diethyl methylformylphosphonate dimethylhydrazone and diethyl ethylformyl-2-phosphonate dimethylhydrazone, contained a protected aldehyde group instead of the usual ester group. A homologation cycle entailed condensation of the reagent with the starting aldehyde, followed by removal of the dimethylhydrazone protective group with a biphasic mixture of 1 M HCl and petroleum ether. This robust two-step process worked with aliphatic, α,β-unsaturated and aromatic aldehydes. Isolated yields for the condensation step ranged from 77% to 89%, and yields for the deprotection step ranged from 81% to 96%. Copyright Taylor & Francis Group, LLC.
- Petroski, Richard J.
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p. 3841 - 3854
(2008/02/10)
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- 1,2-Reduction of α,β-unsaturated hydrazones using dimethylamine-borane/p-toluenesulfonic acid: An easy route to allyl hydrazines
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α,β-Unsaturated hydrazones can be easily converted into N-allyl hydrazines by reaction with dimethylamine-borane/p-toluenesulfonic acid under mild reaction conditions. The reduction works well for N′-allylhydrazides but N′-allyl-N,N-dimethylhydrazines are
- Casarini, Maria E,Ghelfi, Franco,Libertini, Emanuela,Pagnoni, Ugo M,Parsons, Andrew F
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p. 7925 - 7932
(2007/10/03)
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- Transition metal complexes in organic synthesis. Part 57: Synthesis of 1-azabuta-1,3-dienes and application to catalytic complexation of buta-1,3- dienes and cycloalkadienes by the tricarbonyliron fragment
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The 1-azabuta-1,3-dienes 5a-g were prepared and transformed to the corresponding tricarbonyliron complexes 6. The efficiency of 6 as tricarbonyliron transfer reagents and the activity of 5a-g for the catalytic complexation with either nonacarbonyldiiron o
- Kn?lker, Hans-Joachim,Ahrens, Birte,Gonser, Peter,Heininger, Michael,Jones, Peter G.
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p. 2259 - 2271
(2007/10/03)
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- Conversion of Aldehydes into Nitriles via Oxidation of Their Dimethylhydrazones
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The 3-chloroperoxybenzoic acid oxidation of dimethylhydrazones of aromatic aldehydes gives the corresponding nitriles in good yields.Two further examples of the same oxidative transformation of cinnamaldehyde and of hexanal are also given.Except for hexanal hydrazone, all other aldehyde hydrazones can also be efficiently converted into nitriles by treatment with methanolic 30percent hydrogen peroxide in the presence of catalytic amounts of selenium dioxide or, preferentially, 2-nitrobenzeneseleninic acid.
- Said, Samy Bayomy,Skarzewski, Jacek,Mlochowski, Jacek
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p. 223 - 224
(2007/10/02)
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- -Cycloadditionen von α,β-ungesaettigten Hydrazonen. Teil 1. Pyridin-2,3-dicarboximide aus 1-(Dimethylamino)-1,4-dihydropyridin-Derivaten
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Cycloadditions of α,β-Unsaturated Hydrazones to Pyridine-2,3-dicarboximides via 1-(Dimethylamino)-1,4-dihydropyridine Derivatives.The cycloaddition of α,β-unsaturated hydrazones of type 1 (1-aza-1,3-butadienes) with 2-halogenomaleimides 4 affor
- Waldner, Adrian
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p. 486 - 492
(2007/10/02)
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