13466-39-2Relevant academic research and scientific papers
Inverse-electron-demand Diels-Alder reactions of α,β-unsaturated hydrazones with 3-methoxycarbonyl α-pyrones
Hashimoto, Yoshimitsu,Abe, Ryo,Morita, Nobuyoshi,Tamura, Osamu
, p. 8913 - 8916 (2018)
Inverse-electron-demand Diels-Alder reactions of 3-electron-withdrawing group substituted α-pyrones with α,β-unsaturated hydrazones as electron-rich counterparts are catalyzed by Eu(hfc)3 to afford bicyclic lactone cycloadducts. This is an example of umpolung cycloaddition based on functional transformation of carbonyls to hydrazones. A subsequent dehydrazonation reaction enables indirect synthesis of carbonyl group-containing bicyclic lactones, which cannot be easily obtained by the cycloaddition of α-pyrones and enals.
Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
, p. 11232 - 11256 (2013/02/23)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
Synthesis of o -(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes
Dubrovskiy, Anton V.,Larock, Richard C.
supporting information; experimental part, p. 4136 - 4139 (2011/10/12)
A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
Synthesis of β-lactams via cycloaddition of hydrazones with phenoxyketene
Sharma,Pandhi
, p. 2196 - 2200 (2007/10/02)
Phenoxyketene is capable of annelating the disubstituted hydrazones to afford stereoselectivity cis-monocyclic β-lactams with a 1-amino functionality. The ease of cycloaddition is governed by substitutents on the azomethine carbon as well as on the hydraz
New functional Wittig reagent for the formylolefination of aldehydes and ketones
Cristau,Gasc
, p. 341 - 344 (2007/10/02)
Wittig's reagent for n+2 homologation of aldehydes and ketones into α,β-unsaturated aldehydes via the corresponding hydrazones is described.
Synthesis and Reaction of α(Dimethylamino)alkanal Dimethylhydrazones
Habernegg, Renate,Severin, Theodor
, p. 2397 - 2413 (2007/10/02)
Several α(dimethylamino)aldehyde hydrazones of the general structure 11 have been obtained by alkylation of the lithium salt of 9 or by addition of Grignard reagents to 15 or 17.The compounds react with acyl chlorides to give hydrazones of unsaturated aldehydes.The same products 27 are obtained by thermal degradation of the ammonium salts 26.In the hydrazonoammonium salts 26a, g the trimethylammonium group can be substituted by a variety of nucleophiles (--> 34-39).
Preparation of Methine Homologues of Aldehydes and Carboxylic Acids
Zimmermann, Birgit,Lerche, Holger,Severin, Theodor
, p. 2848 - 2858 (2007/10/02)
Dilithium salts of carboxylic acids add to glyoxal mono(dimethylhydrazone) (5) to give salts of β-hydroxy carboxylic acids.Reaction with tosyl chloride affords via decarboxylation the corresponding unsaturated aldehyde hydrazones 10 or 15, which are easily hydrolyzed and oxidized to form unsaturated carboxylic acids.By this method aldehydes and/or carboxylic acids may be extended by one methine group.Extension by three methine groups can be achieved with vinylogous monohydrazones such as 23.
