Synthesis and characterization of coumarin-derived sulfur analogues using Lawesson's reagent
Year: 2025
Type: article
Abstract: The synthesis and characterization of six novel coumarin derivatives containing O and S atoms are described here, namely, ethyl 2-oxo-2H-chromene-3-carboxylate, C12H10O4 (S1a), ethyl 2-sulfanylidene-2H-chromene-3-carboxylate, C12H10O3S (S2a), ethyl 2-sulfanylidene-2H-chromene-3-carbothioate, C12H10O2S2 (S3a), ethyl 8-methoxy-2-oxo-2H-chromene-3-carboxylate, C13H12O5 (S1b), ethyl 8-methoxy-2-sulfanylidene-2H-chromene-3-carboxylate, C13H12O4S (S2b), and ethyl 8-methoxy-2-sulfanylidene-2H-chromene-3-carbothioate, C13H12O3S2 (S3b). Compounds S1a/b were synthesized in good yields following the Knoevenagel condensation method. The thiocarbonyl analogues of these compounds, S2a/b and S3a/b, were obtained using Lawesson's reagent as a thionating compound. The structures of S2a/b and S3a/b were confirmed using FT–IR, 1H and 13C NMR, and UV–Vis spectroscopy, and single-crystal X-ray diffraction. Hirshfeld surface and energy framework analyses show that stacked π–π ring interactions occur for all the structures obtained here, and various hydrogen-bond interactions link the stacks to form three-dimensional energy frameworks.
Institution: Nelson Mandela University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $3,950
OpenAlex ID: W4407946717