One-step synthesis of novel N1-substituted benzimidazole derivatives: Experimental and theoretical investigations

Al Garadi W., SERT Y., El Hafi M., El Ibrahimi B., Ramli Y., Mague J. T., ...More

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.59, no.7, pp.1213-1229, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 7
  • Publication Date: 2022
  • Doi Number: 10.1002/jhet.4461
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), Chimica, EMBASE
  • Page Numbers: pp.1213-1229
  • Yozgat Bozok University Affiliated: Yes

Abstract

In this work, we describe a simple and efficient route for the synthesis of novel N1-substituted benzimidazole derivatives (8-14) by a rearrangement reaction of N1-alkyl-1,5-benzodiazepine-2-thiones (1-7) in the presence of hydroxylamine hydrochloride in boiling ethanol. Good to excellent yields were achieved for a wide range of alkyl partners with both short-chain and long-chain substituents. The title products were identified using H-1 and C-13-NMR spectroscopic measurements and confirmed by single-crystal X-ray diffraction techniques for 8-10. In addition, we performed theoretical studies of 8-10 using Hirshfeld surface analysis, molecular docking studies and, along with experimental data. The predicted spectral data were obtained using density functional theory (DFT) at the B3LYP/6-311++G(d,p) level of theory. Also, according to Monte Carlo simulations, the inhibition trend is 10 > 8 > 9 toward all metals in an acidic environment. Good inhibition performance is predicted for iron as compared to copper and aluminum metals.