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The 1,2,3-Triazole derivatives containing the sulfonyl group have proved their biological importance in medicinal chemistry and drug design. In this sense, we describe the regioselective synthesis of 2-(phenylsulfonyl)-2H-1,2,3-triazole 3 in good yield through a classical sulfonamidation reaction of 1H-1,2,3-triazole 1 with benzenesulfonyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 3 h. This procedure is distinguished by its short reaction time, high yield, excellent regioselectivity, clean reaction profile, and operational simplicity. The sulfonamide 3 was characterized by high-resolution mass spectrometry, FT–IR, UV–Vis, 1D and 2D NMR spectroscopy, and elemental analysis. The sulfonamide 3 exhibited moderate activity against UO-31 renal, SNB-75 central nervous system, HCT-116 colon, and BT-549 breast cancer cell lines, with growth inhibition percentages (GI%) ranging from 10.83% to 17.64%. [ABSTRACT FROM AUTHOR]

• Eco-friendly synthesis of 2-oxo-2 H -chromen-7-yl 4-chlorobenzoate in high yield. • Spectroscopic and thermal analysis were explained. • Crystallographic, Hirshfeld surface, and energy frameworks analyses were performed. • Electrostatic potentials suggest the formation of σ-holes over the Cl atoms. • Anticancer activity was screened against 60 human cancer cell lines. We report the synthesis of the 2-oxo-2 H -chromen-7-yl 4-chlorobenzoate 3 in 94% yield by an O -acylation reaction of 7‑hydroxy-2 H -chromen-2-one 1 and 4-chlorobenzoyl chloride 2 using a slight excess of triethylamine in acetonitrile, heating as fast as possible (AFAP mode) to 60 °C, hold time 5 min, and 600 rpm stirring speed in the Monowave 50 reactor based on conventional heating principles. The structure of the 2-oxo-2 H -chromen-7-yl 4-chlorobenzoate 3 was fully characterized by FT–IR, UV–vis, NMR spectroscopy, mass spectrometry (EI-MS), elemental analysis, thermogravimetry (TG), differential scanning calorimetry (DSC), single-crystal and powder X-ray diffraction. X-Ray diffraction analyses show that compound 3 crystallizes in the Monoclinic, P 2 1 space group. Despite the absence of chiral atoms, the structural restrains imposed by the molecular conformation drive these compounds to crystallize in a Sohncke space group. These results are of great importance in crystal engineering and non-linear optics. In the crystal structure, the packing is controlled mainly by C H‧‧‧O hydrogen bonds. However, Hirshfeld surfaces demonstrated that C H‧‧‧Cl interactions are of great importance. Additionally, electrostatic potentials suggest the formation of σ-holes over the Cl atoms, allowing this atom to behave as a Lewis acid-base. The packing is studied in terms of B3LYP/6-31G(d,p) energy frameworks. Finally, compound 3 showed low activity against MCF7 Breast, SNB-19 Central nervous system, and UO-31 Renal cancer cell lines with a growth inhibition percentage (GI%) ranging from 5.98% to 13.33%. [Display omitted] [ABSTRACT FROM AUTHOR]

The novel N-(3,5-bis(trifluoromethyl)benzyl)stearamide 3 was prepared in moderate yield by a solventless direct amidation reaction of stearic acid 1 with 3,5-bis(trifluoromethyl)benzylamine 2 at 140 °C for 24 h under metal- and catalyst-free conditions. This practical method was conducted in air without any special treatment or activation. The fatty acid amide 3 was fully characterized by IR, UV–Vis, 1D and 2D NMR spectroscopy, mass spectrometry, and elemental analysis. Moreover, molecular electrostatic potential studies, determination of quantum descriptors, fundamental vibrational frequencies, and intensity of vibrational bands were computed by density functional theory (DFT) using the B3LYP method with 6-311+G(d,p) basis set in gas phase. Simulation of the infrared spectrum using the results of these calculations led to good agreement with the observed spectral patterns. [ABSTRACT FROM AUTHOR]