All chromatographic separations were accomplished with
Silica Gel 60N (Kanto Chemical Co., Inc.). Thin-layer chromatography (TLC) was performed with Macherey-Nagel Sil G25 UV
254 pre-coated TLC plates. Reagents were used without further purification unless otherwise specified. Melting points were recorded on a Yanagimoto micro melting point hot-stage apparatus (MP-S3) and are not corrected. IR spectra were recorded on a SHIMADZU
FTIR-8400S spectrophotometer and are reported in frequency of absorption (cm
−1). Only selected IR peaks are reported.
1H NMR (TMS:
δ = 0.00 ppm as an internal standard),
13C NMR (CDCl
3:
δ = 77.00 ppm as an internal standard),
19F NMR (trifluoromethylbenzene:
δ = −64.0 ppm as an external standard) and
77Se NMR (Ph
2Se
2:
δ = 436.15 ppm as an internal standard) spectra were recorded on a JEOL
ECZ-400S (400 MHz, 100 MHz, 376 MHz and 76 MHz) spectrometer in CDCl
3 unless otherwise stated. GC-MS (EI) spectra were recorded on Agilent 5977E Diff-SST MSD-230V spectrometer. HRMS (ESI) were recorded on Agilent
6230 Accurate-Mass TOF LC/MS system. The X-ray diffraction measurements carried out using a Rigaku
XtaLAB Synergy, single source at home/near, HyPix3000 diffractometer. Spectroscopic data of 5-arylselanyluracils 5a, p, q, and 5s are in accordance with the literature.
8,11,13 (link)
Murata Y., Tsuchida S., Nezaki R., Kitamura Y., Matsumura M, & Yasuike S. (2022). Silver-catalyzed three-component reaction of uracils, arylboronic acids, and selenium: synthesis of 5-arylselanyluracils. RSC Advances, 12(23), 14502-14508.