2-thioxo- 3N-(2-methoxyphenyl) −5 [4′-methyl -3′N -(2′-methoxyphenyl) thiazol-2′(3′H)-ylidene] thiazolidin-4-one: Synthesis, characterization, X-ray single crystal structure investigation and quantum chemical calculations

Yahiaoui, Salem; Moliterni, Anna; Corriero, Nicola; Cuocci, Corrado; Toubal, Khaled; Chouaih, Abdelkader; Djafri, Ayada; Hamzaoui, Fodil

doi:10.1016/j.molstruc.2018.09.052

Cited by 19 publications

(6 citation statements)

References 47 publications

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“…The calculated values of the chemical hardness, chemical softness, chemical potential, electronegativity and electrophilicity index of 4b,9b‐dihydroxy‐5‐(4‐chlorophenyl)‐7,7‐dimethyl‐4b,5,7,8‐tetrahydroindeno[1,2‐ b ]indole‐9,10(6H,9bH)‐dione are in agreement compared to other organic molecules . Furthermore, the negative value of the chemical potential suggests the stability of the molecule.…”

Section: Resultssupporting

confidence: 61%

Triflic Acid Functionalized Carbon@Silica Composite: Synthesis and Applications in Organic Synthesis; DFT Studies of Indeno[1,2‐b]indole

Sharma

et al. 2020

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Triflic acid functionalized carbon@silica composite (CStar@SiO2TfOH) was synthesized by the partial carbonization of starch in the presence of silica followed by the immobilization of triflic acid and its catalytic activity was explored for the three component synthesis of hexahydroacridine‐1,8‐diones and indeno[1,2‐b]indole‐9,10‐diones. CStar@SiO2‐TfOH was characterized using different techniques, such as Fourier‐Transform Infrared Spectroscopy (FTIR), Thermogravimetricanalysis (TGA), X‐ray Powder Diffraction (XRD), Energy Dispersive X‐ray (EDX), Scanning Electron Microscopy (SEM) and High Resolution Transmission Electron Microscopy (HR‐TEM) and was found to be recyclable upto five runs without any noticeable change. Further, the intermediate formed during the preparation of hexahydroacridine‐1,8‐dione has been isolated and its structure was confirmed by single crystal X‐ray crystallography which confirms the proposed mechanism. Also, to confirm the structure of 4b,9b‐dihydroxy‐5‐(4‐chlorophenyl)‐7,7‐dimethyl‐4b,5,7,8‐tetrahydroindeno[1,2‐b]indole‐9,10(6H,9bH)‐dione we have performed the DFT study and found that the 1H and 13C chemical shift values and IR wavenumbers predicted by B3LYP method were very close to the experimentally determined values.

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Section: Resultssupporting

confidence: 61%

Triflic Acid Functionalized Carbon@Silica Composite: Synthesis and Applications in Organic Synthesis; DFT Studies of Indeno[1,2‐b]indole

Sharma

et al. 2020

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“…The results of our calculations showed that S1-C5, S1-C1, C1-N1, N1-C2, N1-C4, C6-N2 and O 2-C8 bonds exhibit single bond characteristics, while C4-O2 (1.23 Å) and N2-C1 (1.26 Å) bonds show typical double bond characteristics. 25 The amine N2 atom exhibits a geometry that is typical for an sp 2 rather than an sp 3 atom hybridisation. In addition, the difference in the thiazole ring bonds between theoretical calculation and experimental values does not exceed 0.13 Å.…”

Section: Structure Descriptionmentioning

confidence: 99%

Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

Megrouss

Baara

Boukabcha

et al. 2019

ACSi

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In this paper we report the synthesis and characterization of the (Z)-3-N-(ethyl)-2-N'-((3-methoxyphenyl)imino)thiazolidine-4-one by means of FT-IR, 1 H and 13 C NMR and by single crystal X-ray diffraction. The experimental determination of the crystal structure of the compound has been achieved using X-ray diffraction data. The important characteristic of the structure is the existence of a dihedral angle formed by the benzene and thiazolidinone rings being equal to 86.0° indicating an absence of π-π stacking as well as that the structure is non planar. In the crystal, the molecules are linked by C-H···O and C-H···N hydrogen bonds, these bonds being responsible for the three-dimensional molecular structure packing. In order to compare the experimental results with those of the theoretical calculation, quantum chemical DFT calculations were carried out using B3LYP/6-311G(d,p) basis set. In this context, the molecular electrostatic potential around the molecule and HOMO-LUMO energy levels were also computed. The dipole moment orientations were determined in order to understand the nature of inter-and intramolecular charge transfer. Finally, the stability of the title compound was confirmed throughout the calculation of the chemical reactivity descriptors.

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“…Modified from Ref. [66] Yahiaoui and coauthors [68] described a reliable and simple protocol for the preparation of 2-thioxo-thiazolidin-4-ones 28 by condensation of aromatic amines and CS 2 using NH 4 OH and chloroacetic acid, and the compounds were further treated with CH 3 CN under basic conditions (Scheme 13). The authors also developed a combined experimental and theoretical approach on the molecular struc-…”

Section: Scheme 10mentioning

confidence: 99%

“…Nanjan et al [57] reviewed the antidiabetic activity of thiazolidinone. But there is no detailed review of the synthesis and biological activity of 4 Comparative study of various synthetic protocols [58][59][60][61][62][63][64][65][66][67][68][69] Fig. 5 Comparative study of various synthetic protocols [77][78][79][80][81][82][83][84][85][86] Topics in Current Chemistry (2020) 378:34 1 3 34 Page 8 of 90 hoping to inspire new and even more creative approaches for researchers ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

Sahiba¹,

Sethiya²,

Soni³

et al. 2020

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In past decades, interdisciplinary research has been of great interest for scholars. Thiazolidine motifs behave as a bridge between organic synthesis and medicinal chemistry and compel researchers to explore new drug candidates. Thiazolidine motifs are very intriguing heterocyclic five-membered moieties present in diverse natural and bioactive compounds having sulfur at the first position and nitrogen at the third position. The presence of sulfur enhances their pharmacological properties, and, therefore, they are used as vehicles in the synthesis of valuable organic combinations. They show varied biological properties viz. anticancer, anticonvulsant, antimicrobial, anti-inflammatory, neuroprotective, antioxidant activity and so on. This diversity in the biological response makes it a highly prized moiety. Based on literature studies, various synthetic approaches like multicomponent reaction, click reaction, nano-catalysis and green chemistry have been employed to improve their selectivity, purity, product yield and pharmacokinetic activity. In this review article, we have summarized systematic approaches for the synthesis of thiazolidine and its derivatives, along with their pharmacological activity, including advantages of green synthesis, atom economy, cleaner reaction profile and catalyst recovery which will help scientists to probe and stimulate the study of these scaffolds.

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2-thioxo- 3N-(2-methoxyphenyl) −5 [4′-methyl -3′N -(2′-methoxyphenyl) thiazol-2′(3′H)-ylidene] thiazolidin-4-one: Synthesis, characterization, X-ray single crystal structure investigation and quantum chemical calculations

Cited by 19 publications

References 47 publications

Triflic Acid Functionalized Carbon@Silica Composite: Synthesis and Applications in Organic Synthesis; DFT Studies of Indeno[1,2‐b]indole

Triflic Acid Functionalized Carbon@Silica Composite: Synthesis and Applications in Organic Synthesis; DFT Studies of Indeno[1,2‐b]indole

Synthesis, X-Ray Structure Determination and Related Physical Properties of Thiazolidinone Derivative by DFT Quantum Chemical Method

Saturated Five-Membered Thiazolidines and Their Derivatives: From Synthesis to Biological Applications

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