Copper‐Oxone Promoted Oxidative C−H Functionalization: Synthesis of 2‐Aminobenzothiazoles and Evaluation of Their Antimicrobial Activities

Abstract

Benzothiazole is one of the most important heterocyclic scaffolds existing in both natural and synthetic compounds. This prominent ring is of undoubted interest due to its broad range of therapeutic benefits as well as chemical reactivity in organic reactions. Therefore, we developed a convenient, rapid and efficient methodology for the ring closure reaction of thioureas to form 2-aminobenzothiazole derivatives. We optimized the reaction conditions by trying various catalysts and oxidants. Copper iodide/oxone catalysis provided the best conditions for the preparation of benzothiazoles. The regioselectivity observed in the ring closure reaction of the naphthyl thiourea derivative was investigated and the obtained experimental results were supported by theoretical calculations. In vitro antimicrobial effects of the compounds were tested against various bacterial and fungal strains. Finally, molecular docking studies were carried out to rationalize the achieved biological results and suggest molecular modifications to design new benzothiazole derivatives.

Novel Quinoline-Based Thiosemicarbazide Derivatives: Synthesis, DFT Calculations, and Investigation of Antitubercular, Antibacterial, and Antifungal Activities

“…DFT is used as an excellent theoretical method to identify kinetic and thermodynamic stability and for structural computations, mechanistic insights, molecular interactions, as well as optical and electronic properties of atoms and the molecular system. − All theoretical calculations were carried out with the software package Gaussian 09 . Geometry optimizations of the compounds have been performed using DFT at the B3LYP/6-31+ G­(d,p) level of theory in the gas phase. , Gauss View Rev.…”

AlCl3-Catalyzed Cascade Reactions of 1,2,3-Trimethoxybenzene and Adipoyl Chloride: Spectroscopic Investigations and Density Functional Theory Studies

“…DFT is an excellent computational method for obtaining vibrational frequencies, molecular interactions, and mechanical insights as well as thermodynamic and kinetic stability. − This computational method is also used with hybrid functionals to calculate the structural, optical, and electronic properties of molecular systems and atoms. − All computations were performed with the software package Gaussian 09W and carried out by DFT using B3LYP (Becke’s three parameter hybrid functional combined with the Lee–Yang–Parr correlation functional) , and M06-2X , hybrid functionals with the 6-311+G­(d,p) basis set in the gas phase. The results were visualized using the software GaussView 5 and CYLview v1.0.561 BETA for data preparation and visualization of the results .…”

Investigation of cholinesterase and α-glucosidase enzyme activities, and molecular docking and dft studies for 1,2-disubstituted cyclopentane derivatives with phenyl and benzyl units

“…DFT is an excellent method often used to describe molecular structure and stability, mechanistic insights, and molecular interactions. [54][55][56][57][58][59] In our previous study, DFT studies including structural properties, natural bond orbital analysis of donoracceptor interactions, charges on the atoms, comparison of intramolecular hydrogen bonds, and quantum chemical reactivity identi ers for compounds 4-9 were performed using two functional levels, B3LYP and M06-2X, and examined in detail [7]. Moreover, the experimental 1 H and 13 C NMR chemical shifts were compared with the calculated values.…”