200802-52-4Relevant academic research and scientific papers
Lewis acid-mediated defluorinative [3+2] cycloaddition/aromatization cascade of 2,2-difluoroethanol systems with nitriles
Hsieh, Min-Tsang,Lee, Kuo-Hsiung,Kuo, Sheng-Chu,Lin, Hui-Chang
, p. 1605 - 1610 (2018/03/05)
The properties of C?F bonds, including high thermal and chemical stability, make derivatization of organic fluorine-containing compounds by the activation of the C?F bond and subsequent functionalization quite challenging. We herein report a Lewis acid-mediated defluorinative cycloaddition/aromatization cascade of 2,2-difluoroethanols with nitriles as a novel synthetic method for the preparation of 2,4,5-trisubstituted oxazoles. This reaction, which involves cleavage of two C?F bonds and the consecutive formation of C?O and C?N bonds in a one-pot fashion, features a broad substrate scope and moderate to high reaction yields. Mechanistic studies revealed that the reaction is initiated by the Lewis acid-mediated ring closure of the 2,2-difluoroethanol to produce the fluoroepoxide intermediate. (Figure presented.).
Synthesis, structure, and photophysical properties of polyarylated imidazoles and oxazoles
Buttke, Klaus,Baumgaertel, Helmut,Niclas, Hans-Joachim,Schneider, Matthias
, p. 721 - 728 (2007/10/03)
23 tetraphenylimidazoles 1,2 and 11 triphenyl-oxazoles 4,5 with amino, nitro, methoxy, hydroxy, or halogeno substituants chiefly in the para position were prepared. The absorption and fluorescence emission properties were investigated in ethanolic solution. The effects of the substituents in 1,2 on the spectral shifts show that the arrangement of the phenyl rings in 1 position is not coplanar in relation to the heterocycle whereas the phenyl rings in 2 position are more coplanar. The spectral changes of compound 2a in solvents of various polarity (dielectric constants 2,02-47,24) are almost negligible. The Stokes shift is moderately increased. A remarkable increase in the fluorescence quantum yield is observed by chlorine substitution in phenyl ring 2.
