A novel and efficient amidation of 2-aminothiazole

Choi, Minho; Won, Sun-Woo; Jo, Hyeju; Seo, Seung‐Yong; Lee, Yeon-Ju; Lee, Hyi‐Seung; Lee, Heesoon; Hong, Jin Tae; Kwak, Young‐Shin

doi:10.1016/j.tetlet.2014.10.031

Cited by 5 publications

(5 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The H6 proton coupled to the H5 proton resonated as a doublet peaks at 7.06 ppm. These data agree with proton values of the reported similar compounds (Yakan et al, 2020;Choi et al, 2014;Kerdphon et al, 2015).…”

Section: Nmr Spectra 1 H Nmr Spectrasupporting

confidence: 92%

“…The C1, C2, C3 C4, C6, C7, C8, and C9 carbon atoms were resonated 138.60, 130.24, 127.69, 128.41, 140.71, 126.29, 126.94, and 125.36 ppm, respectively. These data agree with proton values of the reported similar compounds (Yakan et al, 2020;Choi et al, 2014;Kerdphon et al, 2015). Supporting information, sup-7…”

Section: Nmr Spectrasupporting

confidence: 90%

“…The products were obtained by slightly modifying the reported method of Mazik et al (1999). All spectra (IR and 1 H/ 13 C NMR) of (I) are presented in the supporting information and the obtained spectral results are in agreement with values of similar compounds reported previously in the literature (Yakan et al, 2020;Kerdphon et al, 2015;Choi et al, 2014;Iriarte et al, 2008).…”

Section: Synthesis and Crystallizationsupporting

confidence: 83%

See 2 more Smart Citations

Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide

Çakmak

Demi̇rci̇oğlu

Uzun

et al. 2022

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

In the present study, N-(thiophen-2-ylmethyl)thiophene-2-carboxamide, C10H9NOS2, (I), was obtained by the reaction of thiophene-2-carbonyl chloride and thiophen-2-ylmethanamine. Characterization of (I) was carried out using X-ray diffraction, spectroscopic techniques and elemental analyses. The DFT/B3LYP/6-311++G(d,p) theoretical level was successfully applied to calculate the optimized geometry and the local and global chemical activity parameters. The results obtained show good agreement between the experimental and theoretical geometrical parameters. The local and global chemical activity parameters were examined to determine the electrophilic and nucleophilic sites in (I). The natural bond orbital (NBO) analysis of (I) gives an efficient methodology for investigating the inter- and intramolecular bonding, as well as giving a convenient basis for investigating charge transfer or conjugative interactions in molecular systems. Also, the antimicrobial activity of (I) was investigated against eight microorganisms using the microdilution method and it is found to have an effective antibacterial activity. In addition, molecular docking studies were calculated in order to understand the nature of the binding of (I) with a lung cancer protein (PDB entry 1x2j).

show abstract

Section: Nmr Spectra 1 H Nmr Spectrasupporting

confidence: 92%

Section: Nmr Spectrasupporting

confidence: 90%

Section: Synthesis and Crystallizationsupporting

confidence: 83%

See 1 more Smart Citation

Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide

Çakmak

Demi̇rci̇oğlu

Uzun

et al. 2022

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

show abstract

“…In the same study, the aromatic protons (H4 and H5) of the thiazole ring were observed at 7.53-7.03 ppm (Yakan et al, 2020). These data agree with proton values reported for similar compounds (Kos ¸ar Kırca et al, 2020;Yakan et al, 2020;Choi et al, 2014;Kerdphon et al, 2015).…”

Section: H Nmr Spectrasupporting

confidence: 88%

“…In the same study, the C5-C7 atoms of the thiazole ring were observed at 153.1, 138.9 and 130.6 ppm, respectively(Yakan et al, 2020). These results are consistent with values reported for similar compounds (Rubio-Pe ´rez et al, 2012;Yakan et al, 2020;Choi et al, 2014;Kerdphon et al, 2015).…”

supporting

confidence: 89%

Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity

Çakmak¹,

Kırca²,

Veyisoglu³

et al. 2022

Acta Crystallogr C Struct Chem

View full text Add to dashboard Cite

A thiazole-based heterocyclic amide, namely, N-(thiazol-2-yl)furan-2-carboxamide, C8H6N2O2S, was synthesized and investigated for its antimicrobial activity. The structure was characterized by elemental analysis and IR, 1H NMR, and 13C NMR spectroscopy. The molecular and electronic structures were investigated experimentally by single-crystal X-ray diffraction (XRD) and theoretically by density functional theory (DFT) modelling. The compound crystallized in the monoclinic space group P21/n and the asymmetric unit contains two symmetrically independent molecules. Several noncovalent interactions were recorded by XRD and analysed with Hirshfeld surface analysis (HSA) calculations. Natural bond orbital, molecular electrostatic potential, second-order nonlinear optical and thermodynamic property analyses were also carried out using the DFT/B3LYP method. The title compound was evaluated for antimicrobial activity against eight microorganisms consisting of Gram-negative bacteria, Gram-positive bacteria and fungi. The compound showed good antimicrobial activity against the eight tested microorganisms. This suggests that the compound merits further study for potential pharmacological and medical applications.

show abstract

ChemInform Abstract: A Novel and Efficient Amidation of 2‐Aminothiazole.

Jung

2015

ChemInform

View full text Add to dashboard Cite

show abstract

A novel and efficient amidation of 2-aminothiazole

Cited by 5 publications

References 27 publications

Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide

Synthesis, X-ray structure, antimicrobial activity, DFT and molecular docking studies of N-(thiophen-2-ylmethyl)thiophene-2-carboxamide

Experimental and theoretical investigations on a furan-2-carboxamide-bearing thiazole: synthesis, molecular characterization by IR/NMR/XRD, electronic characterization by DFT, Hirshfeld surface analysis and biological activity

ChemInform Abstract: A Novel and Efficient Amidation of 2‐Aminothiazole.

Contact Info

Product

Resources

About