Ghlf plates

¹H and ¹³C NMR spectra were recorded on a Bruker 400 MHz spectrometer using tetramethylsilane (TMS) as an internal standard. Peak positions are given in parts per million (δ). Purity of each of the final, tested compounds was determined by HPLC on a Shimadzu LC-20AB (Solvent system; 55% MeCN/40% H₂O, isocratic; Column: Shimadzu C18, 50 μm, 50 x 4.6 mm) and was ≥95% (UV, 254 nm). The HRMS spectra were recorded on a Shimadzu LCMS-IT-TOF, and the molecular weight of the compounds was within 0.05% of calculated values. Flash chromatography was performed using silica gel (230–400 mesh). All reactions were monitored by thin-layer chromatography (TLC) on silica gel GHLF plates (250 μm, Macherey-Nagel, Inc., Bethlehem, PA). Compounds 7, 8, and 12a were synthesized according to previously reported literature [33 (link),34 (link),39 ]. It should be noted that aminonaphthalenes are generally carcinogenic in nature. Caution should be used while handling them.

¹H and ¹³C NMR spectra were recorded on a Bruker AVIII and AVIII HD 400 spectrometers equipped with a room temperature 5 mm broadband observe (BBO) probes with z-gradient. Chemical shifts were reported in parts per million (δ) using either tetramethylsilane (TMS) or the undeuterated residual solvent peak as an internal standard (CDCl₃: ¹H δ = 7.26 and ¹³C δ = 77.2; CD₃COCD₃: ¹H δ = 2.05 and ¹³C δ = 29.2; CD₃OD: ¹H δ = 3.31 and ¹³C = 49.2; CD₃CN: ¹H δ = 1.96and ¹³C δ = 118.3; DMSO-d₆: ¹H δ = 2.50 and ¹³C δ = 39.5). Purity of each of the final, tested compounds was determined by HPLC on a Shimadzu LC-20AB (Solvent system; MeCN/H₂O, 0.1% Formic Acid; Column: Shimadzu C18, 50 μm, 50 × 4.6 mm) and was ≥95% (HPLC Method: 15:85 MeCN:H₂O, 0–2 min; 15:85 – 95:5 MeCN:H₂O, linear gradient, 2 – 9 min; 95:5 MeCN:H₂O, 9–10.7 min; 95:5 – 15:85 MeCN:H₂O, linear gradient, 10.7 – 11 min; 15:85 MeCN:H₂O, 11 – 13 min. UV, 254 nm). The HRMS spectra were recorded on a Shimadzu LCMS-IT-TOF. Flash chromatography was performed on a Teledyne-Isco Combiflash Rf+ system using preloaded silica gel cartridges (230–400 mesh). Reactions were monitored by thin-layer chromatography (TLC) on silica gel GHLF plates (250 μm, Macherey-Nagel, Inc.).