Eco-Friendly Synthesis of 3-Aryl-2,3-dihydro-1,3,4-thiadiazoles Based on Benzofuran and Chromone Moieties

Abstract

In consideration of green and efficient organic chemical methodology, we reported here a green, an efficient and convenient procedure for synthesis of 3-aryl-2,3-dihydro-1,3,4-thiadiazoles based on benzofuran as well as chromone moieties, using the grinding technique. Condensation of 1-(4,7-dimethoxybenzofuran-5-yl)ethan-1-ones 2, 3; 7-hydroxy-5-methoxy-2-methyl-4-oxo-4H-chromene-6-carbaldehyde (4); and 4-oxo-4H-chromene-3-carbaldehydes 10a–c with alkyl hydrazine carbodithioates followed with some hydrazonoyl halides 7a–g under grinding and solvent-free condition led to the formation of the targeted 3-aryl-2,3-dihydro-1,3,4-thiadiazoles 8a–g, 9a,b, and 12a–f, correspondingly. Structures of the synthesized compounds were clarified based on their elemental analyses and spectral data. Eleven of the entire target compounds were selected for anticancer activity against 60 human cancer cell lines at a single dose (10‾⁵ M) by the National Cancer Institute (NCI, Bethesda, USA).

Keywords:

• Anti-cancer
• benzofuran
• chromone;green chemistry
• solvent free
• thiadiazole

Disclosure statement

The authors declare no conflicts of interest.

Author contribution

Anhar Abdel-Aziem and Eslam R. El-Sawy, conceptualization, methodology, data interpretation, and writing-original draft preparation; Gilbert Kirsch, writing-review and editing the final draft.

Additional information

Funding

This work was supported by grant from the French Embassy in Egypt (Institut Français d’Egypte) and Université de Lorraine, Laboratoire Lorrain de Chimie Moléculaire (L.2.C.M.), Metz, France.