84417-34-5Relevant academic research and scientific papers
Combination of Metal-Catalyzed Cycloisomerizations and Biocatalysis in Aqueous Media: Asymmetric Construction of Chiral Alcohols, Lactones, and γ-Hydroxy-Carbonyl Compounds
Rodríguez-álvarez, María J.,Ríos-Lombardía, Nicolás,Schumacher, S?ren,Pérez-Iglesias, David,Morís, Francisco,Cadierno, Victorio,García-álvarez, Joaquín,González-Sabín, Javier
, p. 7753 - 7759 (2017/11/10)
The combination of the metal-catalyzed cycloisomerization of alkynes containing a tethered nucleophile as substituent in aqueous media (followed by the spontaneous hydrolysis, hydroalkoxylation, or aminolysis of the transiently formed five-membered heterocycles) with the subsequent enantioselective ketone bioreduction (mediated by KREDs) has been achieved. The overall transformations, which formally involve a three-step one-pot reaction, provide a variety of enantiopure valuable molecules (e.g., 1,4-diols, lactones, and γ-hydroxy-carbonyl compounds (carboxylic acids, esters, and amides)) with high conversions and enantioselectivities and under mild reaction conditions, disclosing the concept of integrated metal-catalyzed cycloisomerizations of alkynes and enzymatic catalysis in water.
Br?nsted Acid-Catalyzed Three-Component Reaction of Anilines, α-Oxoaldehydes, and α-Angelicalactone for the Synthesis of Complex Pyrrolidones
Huo, Congde,Yuan, Yong
, p. 12704 - 12710 (2016/01/09)
A green and efficient three-component reaction of easily available anilines, α-oxoaldehydes, and α-angelicalactone was developed for the synthesis of highly functionalized pyrrolidones using dilute sulfuric acid as the catalyst. Products were obtained in good to high yields at room temperature and under solvent-free conditions. The reaction could also be performed on a multigram scale with the same efficiency.
Conjugates of Catecholamines. 1. N-Alkyl-Functionalized Carboxylic Acid Congeners and Amides Related to Isoproterenol
Jacobson, Kenneth A.,Marr-Leisy, Debra,Rosenkranz, Roberto P.,Verlander, Michael S.,Melmon, Kenneth L.,Goodman, Murray
, p. 492 - 499 (2007/10/02)
A series of functionalized catecholamines (congeners) has been synthesized in which, formalistically, N-isopropyl group of isoproterenol has been extended by a linear alkyl chain of varying length, terminated by a carboxy group or a substituted amide.The compounds were prepared generally via the reductive amination of norepinephrine with a keto acid or a preformed keto amide.An alternate synthesis of the model amide derivatives, involving activation of the carboxylic acid congeners and coupling with amines, was complicated in the case of short-chain derivatives by facile cyclization to lactams.In vitro evaluation of these compounds as potential β-adrenergic agonists has shown that, while the carboxylic acid congeners have relatively low potencies, the model amide derivatives have potencies that are highly dependent on both the length of the alkyl chain and also the nature of the substituent on the amide.In general, aromatic amides are the most potent, although the nature and position of substituents on the aromatic group dramatically influences their potency.The implications of these studies, in terms of general β-adrenergic drug design and also the attachment of the carboxylic acid congeners to carries, are discussed
Synthesis of Spirooxazolidinones
Subbaraj, A.,Ramakrishnan, V. T.
, p. 506 - 513 (2007/10/02)
α-Chloro-N-arylacetamides (3) react with 2-methylcyclohexane-1,3-dione, 2-ethylcyclohexane-1,3-dione and 2,5,5-trimethylcyclohexane-1,3-dione to give the respective 4-aryl-spirooxazolidinones.An intermediate, 2-(2,5,5-trimethyl-3-oxocyclohexen-1-yloxy)-N-(p-tolyl)acetamide, has been isolated establishing the suggested mechanism of formation of the spirooxazolidinones.Also, general mass spectral fragmentation pattern is discussed.
