Renaissance of 4-(5-nitrofuran-2-yl)-5-arylamino substituted pyrimidines: microwave-assisted synthesis and antitubercular activity

The Buchwald–Hartwig cross-coupling of 5-bromo-4-(furan-2-yl)pyrimidine with various anilines afforded the corresponding new 5-(arylamino)pyrimidines, the reaction being accelerated by microwave irradiation. Most of the obtained compounds proved to possess a high bacteriostatic in vitro effect against Mycobacterium tuberculosis H Rv, Neisseria gonorrhoeae, and Staphylococcus aureus including Methicillin-resistant strain, which is stronger than that of the commercial drug Spectinomycin. 3

V-Shaped Methylpyrimidinium Chromophores for Nonlinear Optics

International audienceA series of four V-shaped methylpyrimidinium salts bearing diphenylamino-electron-donating groups appended at various pyrimidine positions were designed. These chromophores were obtained by regioselective N(1) monomethylation by methyl methanesulfonate of the pyrimidine core. Linear optical properties were studied experimentally and electronic properties were further completed by (TD)-DFT calculations. The second-order nonlinear optical (NLO) properties were also studied using electric field induced second harmonic generation (EFISH) method in chloroform, and all pyrimidinium salts exhibited μβ(0) >1000×10(-48)  esu. The 2,4-disubstituted pyrimidinium core is preferred over 4,6-disubstitution as it enhances the NLO response and increases the dipole moment. (E,E)-2,4-Bis[4-(diphenylamino)styryl]-1-methylpyrimidin-1-ium methanesulfonate appears to be the best NLO-phore in chloroform in the series (μβ(0) =2500×10(-48)  esu) and a figure of merit μβ(0) /MW=3.4 10(-48)  esu mol g(-1)

(<i>E</i>)-2-(6-(4′-(Diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5(4<i>H</i>)-ylidene)-2-(6-(4′-(diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5-yl)acetonitrile

[1,2,5]Oxadiazolo[3,4-b]pyrazines are of great interest due to their promising photophysical and electrochemical properties, as well their potential use in a wide range of electronic devices. Herein, we report on the preparation of the unexpected product derived from the interaction of 2′-([1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-N,N-diphenyl-[1,1′-biphenyl]-4-amine with 2-cyanoacetic acid under basic conditions. The resulting product was characterized using 1H and 13C NMR spectra, high resolution mass spectrometry, Fourier-transform infrared spectroscopy (FTIR), and X-ray diffraction analyses. Furthermore, its photophysical and electrochemical properties were studied using cyclic voltammetry, UV–Vis, and emission spectroscopy. The experimental results have been further rationalized through theoretical DFT calculations