Refernces
10.1039/c2cc32823b
The research aimed to develop an enantioselective metallo-organocatalyzed method for the preparation of cyclopentanes that incorporate an all-carbon quaternary stereocenter, a significant challenge in organic chemistry due to the steric repulsion between the four carbon substituents. The researchers employed a cooperative catalytic strategy that combined aminocatalysis with a chiral copper(I) complex, leading to the enantio-enriched formation of cyclopentanes. Key chemicals used in this process included formyl-alkynes, chiral phosphorus ligands (A–F), copper(II) trifluoromethanesulfonate, cyclohexylamine, and various substrates such as gem-dimethylmalonate, gem-dimethoxymethyl, and gem-dibenzyloxymethyl groups. The study concluded that the cooperative enamine catalysis and copper(I)-4-MeO-3,5-(t-Bu)2-MeO-BIPHEP activation of alkynes resulted in enantioenriched cyclopentane carbaldehydes with moderate to excellent enantioselectivities, demonstrating the efficiency of this novel metallo-organocatalytic approach for constructing all-carbon quaternary stereogenic centers.
10.1016/j.bmcl.2009.04.125
The research aimed to develop new selective COX-2 inhibitors to treat inflammation and inflammation-associated disorders with reduced gastrointestinal toxicities compared to traditional NSAIDs. The study focused on synthesizing a new group of 3-alkyl-2-aryl-1,3-thiazinan-4-one derivatives with a methylsulfonyl pharmacophore and evaluating their COX-2 inhibitory activity. Key chemicals used in the synthesis included amines (such as benzylamine, phenethylamine, and cyclohexylamine), 4-methylthiobenzaldehyde, and thioglycolic acid. The most potent and selective COX-2 inhibitor identified was 3-benzyl-2-(4-methylsulfonylphenyl)-1,3-thiazinan-4-one (11a), with an IC50 of 0.06 μM and a selectivity index of 285.8. Molecular modeling suggested that the compound's potent and selective inhibitory activity was due to its specific interactions with the COX-2 active site. The study concluded that these derivatives could serve as promising candidates for the development of new anti-inflammatory drugs with fewer gastrointestinal side effects.
10.1021/jo00364a038
The study explores the synthesis of vinylketenes via the thermolysis of 3-azido-1,2-benzoquinones. Key chemicals include 3-azido-4,6-di-tert-butyl-1,2-benzoquinone, which upon thermolysis in refluxing benzene, yields the stable ketene 9. This ketene reacts with methanol to form esters 10 and 11, and with cyclohexylamine to produce amide 12. Another azidoquinone, 13, thermolyzed in the presence of ethanol or ethoxypropyne, generates ester 15 and cyclohexadienone 16, respectively. However, azidoquinone 17 cyclizes to indoloquinone 18 instead of fragmenting to a ketene. The study also details the synthesis of dichloroquinones 23 and 24, which serve as precursors to azidoquinones 13 and 17. The research highlights the potential of this method for synthesizing vinylketenes and identifies limitations, such as the cyclization observed with azidoquinone 17.
10.1021/jo00051a017
The research investigates the oxidation of various primary amines using dimethyldioxirane (1) and in situ oxidations with oxone. The study explores the formation of different products such as oximes, nitroso dimers, nitroalkanes, nitrones, and oxaziridines under various reaction conditions. Key chemicals involved include cyclohexylamine (2a), n-butylamine (2b), benzylamine (2c), n-decylamine (2d), and 5-methyl-3,4-hexadienylamine (2e). The reactions were performed in solvents like acetone and dichloromethane, with reagents such as NaHCO3 and K2CO3 used as buffering agents. The products were analyzed using techniques like NMR, GC, and MS. The study aims to understand the competing processes and optimize the conditions for specific oxidative transformations of primary amines.
C
C:Corrosive;
