Synthesis, crystal structure and vibrational properties of N-(8-(3-(3-(tert-butyl)ureido)phenyl)imidazo[1,2-a]pyridin-6-yl)acetamide

Derivatives of imidazo[1,2a]pyridine, a type of fused heterocyclic substance, play major roles in the chemical fields and are confirmed to be the core fragments of various drug molecules. In this study, the title compound was designed and synthesized from the coupling reaction of N-(8-iodoimidazo[1,2-a]pyridin-6-yl)acetamide and 1-(tert-butyl)-3-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea. The crystals of the title compound were obtained by solvent evaporation at room temperature. The structure of N-(8-(3-(3-(tert-butyl)ureido)phenyl)imidazo[1,2-a]pyridin-6-yl)acetamide was demonstrated by H-1 NMR, C-13 NMR, FT-IR and single crystal X-ray diffraction studies. Additionally, theoretical calculations, based on the density functional method B3LYP at the 6-311 + G(d, p) level, were performed on the title compound, and the molecular structure optimized using DFT was consistent with the results obtained using X-ray diffraction. In addition, hydrogen bonding, intramolecular pi-pi stacking and the Van der Waals forces significantly stabilized of N-(8-(3-(3-(tert-butyl)ureido)phenyl)imidazo[1,2- a]pyridin-6-yl)acetamide, as shown in the packing diagram. Moreover, the vibrations of the title compound were reliably assigned on the basis of characteristic vibrational absorption bands. Finally, frontier molecular orbital (FMO) was employed to verify the charge transfer interaction involving the electron acceptor and electron donor groups. (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

Derivatives of imidazo[1,2a]pyridine, a type of fused heterocyclic substance, are shown to be crucial in chemical fields and as core fragments in drug molecules. In this study, a new compound was designed and synthesized, and its structure and stability were characterized using various analytical techniques, along with verification of charge transfer interactions.