1075-70-3Relevant articles and documents
Preparation and deprotection of aldehyde dimethylhydrazones
Petroski, Richard J.
, p. 1727 - 1734 (2006)
Aldehydes were conveniently protected as dimethylhydrazones by stirring a mixture of the aldehyde, N,N-dimethylhydrazine, anhydrous magnesium sulfate, and dichloromethane at room temperature. Azeotropic removal of water, formed during the course of the reaction, was not required because anhydrous magnesium sulfate functions as a water scavenger. Deprotection of aldehyde dimethylhydrazones was accomplished by stirring a mixture of the aldehyde dimethylhydrazone and aqueous glyoxylic acid at room temperature. The reaction time for the preparation and deprotection of aldehyde dimethylhydrazones varied with the structure of the aldehyde. Copyright Taylor & Francis Group, LLC.
An alternative channel of reductive condensation of trichloromethylarenes with hydrazines
Belen'kii,Luiksaar,Chuvylkin,Krayushkin
, p. 886 - 893 (2000)
The reductive condensation of trichloromethylarenes with hydrazines can proceed without intermediate formation of pyridinium salts and without participation of pyridine in the reduction act. Variants of reductive condensation using hydrazines as reducting agents and α-chlorobenzylhydrazines and hydrazonoyl chlorides, nitrite imines, or hydrazonoylpyridinium salts as intermediates are considered. α-Chlorobenzylhydrazines and hydrazonoyl chlorides are shown to be the most probable intermediates.
Design, synthesis, and evaluation of analogues of 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide as orally available general anesthetics
Choudhury-Mukherjee, Indrani,Schenck, Hilary A.,Cechova, Sylvia,Pajewski, Thomas N.,Kapur, Jaideep,Ellena, Jeffrey,Cafiso, David S.,Brown, Milton L.
, p. 2494 - 2501 (2003)
We have recently discovered a novel class of compounds that have oral general anesthetic activity, potent anticonvulsant activity, and minimal hemodynamic effects. The 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide (1) demonstrated potent ability to reduce the minimum alveolar concentration (MAC) of isoflurane, with no effects on heart rate or blood pressure at therapeutic concentrations. Analogue 1 also had potent oral anticonvulsant activity against maximal electroshock (MES) and subcutaneous metrazol (scMET) models with a therapeutic index of 10 for MES activity. In this study, we further synthesized nine new racemic analogues and evaluated these compounds for effects on isoflurane MAC reduction and blood pressure. Preliminary data demonstrate potent reduction in the isoflurane MAC for two new compounds. Current mechanistic studies were unrevealing for effects on voltage-gated ion channels as a putative mechanism. Liposomal partitioning studies using 19F NMR reveal that the aromatic region partitions into the core of the lipid. This partitioning correlated with general anesthetic activity of this class of compounds. Further, compound 1 was used at a concentration of 1 mM and slightly enhanced GABAA current in hippocampal neurons at 10 μM. Altogether, 3,3,3-trifluoro-2-hydroxy-2-phenyl-propionamide exhibited excellent oral general anesthetic activity and appears devoid of significant side effects (i.e., alterations in blood pressure or heart rate).
Efficient reductions of dimethylhydrazones using preformed primary amine boranes
Frabitore, Christian,Lépeule, Jérome,Livinghouse, Tom,Robinson, William C.,Towey, Bradley
supporting information, (2021/12/21)
A convenient method for the reduction of N,N-dimethylhydrazones using amine borane complexes generated in situ is described. It was found that primary amine borane complexes performed exceedingly well at reducing N,N-dimethylhydrazones in as little as 1.1 equivalents, furnishing the corresponding air-sensitive hydrazine products in excellent yields.
AROMATIC COMPOUNDS FROM FURANICS
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Page/Page column 34, (2017/09/21)
Described are methods for preparing phenols, benzene carboxylic acids, esters and anhydrides thereof from furanic compounds by reaction with a dienophile, wherein the furanic compounds are reacted with a hydrazine and/or oxime and then reacted with a dienophile.
