62375-98-8Relevant articles and documents
Enolization rates control mono-: Versus di-fluorination of 1,3-dicarbonyl derivatives
Rozatian, Neshat,Beeby, Andrew,Ashworth, Ian W.,Sandford, Graham,Hodgson, David R.W.
, p. 10318 - 10330 (2019/11/20)
Fluorine-containing 1,3-dicarbonyl derivatives are essential building blocks for drug discovery and manufacture. To understand the factors that determine selectivity between mono- and di-fluorination of 1,3-dicarbonyl systems, we have performed kinetic studies of keto-enol tautomerism and fluorination processes. Photoketonization of 1,3-diaryl-1,3-dicarbonyl derivatives and their 2-fluoro analogues is coupled with relaxation kinetics to determine enolization rates. Reaction additives such as water accelerate enolization processes, especially of 2-fluoro-1,3-dicarbonyl systems. Kinetic studies of enol fluorination with Selectfluor and NFSI reveal the quantitative effects of 2-fluorination upon enol nucleophilicity towards reagents of markedly different electrophilicity. Our findings have important implications for the synthesis of α,α-difluoroketonic compounds, providing valuable quantitative information to aid in the design of fluorination and difluorination reactions.
Preparation of β-keto esters and β-diketones by C-acylation/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles
Katritzky, Alan R.,Wang, Zuoquan,Wang, Mingyi,Wilkerson, Chavon R.,Hall, C. Dennis,Akhmedov, Novruz G.
, p. 6617 - 6622 (2007/10/03)
Acyl-, aroyl-, and heteroaroyl-acetic esters 6a-f and 8a-1 are prepared by reactions of 1-acylbenzotriazoles 1a-k with acetoacetic esters 5 or 7a,b in the presence of sodium hydride followed by regioselective deacetylation. Similar C-acylation/deacetylati
