Synthesis and Structures of Fluoroalkylated Triketides

Abstract

The synthesis and structures of fluoroalkylated triketides (3,5-dioxo esters) and 1,3,5-triketones -such as 1,1,1-trifluoroheptane-2,4,6-dione -were studied. The synthesis is based on reactions between 1,3-dicarbonyl dianions and esters. In CDCl 3 , the fluoroalkylated triketides exclusively exist in the forms of enol tautomers. In [D 6 ]DMSO, equilibria between enols and keto hydrates, formed by addition of water to the

Synthesis and Solution Structure of 1H‐Benzo‐1,5‐diazepine Derivatives with a Perfluoroalkyl Side Chain

“…Perfluorinated 3,5‐dioxoesters 1a – f were prepared, as previously reported , by reaction of the dianions of ethyl acetoacetate or ethyl 2‐chloroacetoacetate with the corresponding perfluorinated esters ( Scheme ).…”

“…Yachevskii and co‐workers described the cyclocondensation of 1,2‐diaminobenzene with unsymmetrical perfluorinated 1,3,5 ‐ triketones . We have recently reported the synthesis of perfluorinated 3,5‐dioxoesters and their application to the synthesis of pyrazoles and isoxazoles . Herein, we wish to present, to the best of our knowledge, the first cyclocondensation reactions of perfluorinated 3,5‐dioxoesters with 1,2‐diaminobenzenes.…”

2-Aryl-6-Polyfluoroalkyl-4-Pyrones as Promising RF-Building-Blocks: Synthesis and Application for Construction of Fluorinated Azaheterocycles

“…Despite the promising synthetic utility of CF 3 -bearing 4-pyrones, they remain to be hard-to-reach compounds [ 17 , 18 ]. The methods for the construction of 4-pyrones are actively developed, and in the literature there are three general approaches for the synthesis of 2-R F -4-pyrones based on (i) cyclization of tricarbonyl compounds or their derivatives prepared via Claisen condensation [ 19 , 20 , 21 , 22 ], (ii) cycloadditions of ketenes [ 23 , 24 , 25 ], and (iii) modification of substituted 2-R F -4-pyrones (usually for carboxylic acid derivatives) via side-chain transformations [ 26 ] ( Scheme 1 ). However, there are usually some limitations connected with the narrow scope of obtained pyrones, variation of the nature of the substituents in several positions of the pyrone ring, and preparation of 4-pyrones bearing long-chain polyfluoroakyl substituents.…”

A Convenient Approach to CF3‐Containing N‐Heterocycles Based on 2‐Methoxy‐2‐methyl‐5‐(trifluoromethyl)furan‐3(2H)‐one

“…For example, 3‐CF 3 ‐pyrazoles 4 and 5 have been obtained from the corresponding 1,3,5‐triketones and 4‐pyran‐4‐ones, respectively (Figure 1). 7e,8…”