Camphor sulfonic acid catalyzed a simple, facile, and general method for the synthesis of 2-arylbenzothiazoles, 2-arylbenzimidazoles, and 3<i>H</i>-spiro[benzo[<i>d</i>]thiazole-2,3′-indolin]-2′-ones at room temperature

Kaur, Gurpreet; Moudgil, Radha; Shamim, Mussarat; Gupta, Vivek K.; Banerjee, Bubun

doi:10.1080/00397911.2020.1870043

Cited by 26 publications

(5 citation statements)

References 122 publications

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“…The reaction of 1 with PCC in EtOAc led to the mono-oxidation of the 3-methyl group to afford 3-formyl-8-phenyl-BODIPY (2) in 67% yield [52]. The aldehyde 2 was then reacted with 1,2-aminothiophenol in the presence of TsOH in anhydrous DMF at 72 • C to afford 3-benzothiazole-8-phenyl-BODIPY (TC497) in 52% yield [53] (Scheme 1). Subsequently, functionalization of TC497 at C6 was pursued to investigate the effect of additional substituents at this position of the 8-phenyl-BODIPY scaffold.…”

Section: Chemistrymentioning

confidence: 99%

A Study on the Structure, Optical Properties and Cellular Localization of Novel 1,3-Benzothiazole-Substituted BODIPYs

Kirkilessi,

Arapatzi,

Reis

et al. 2023

Colorants

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A library of seven novel 1,3-benzothiazole-substituted BODIPY derivatives with tunable optical properties was synthesized. The new fluorescent dyes exhibited bathochromically shifted absorptions (up to 670 nm) and emissions centered in the red and near-infrared spectral region (up to 677 nm) in comparison to the parent compound 8-phenyl BODIPY (λabs: 499 nm, λemi: 508 nm). (TD)DFT calculations were performed to rationalize the spectroscopic properties of the new dyes. The cellular biodistribution of the new BODIPY dyes, their fluorescence stability and toxicity were investigated in both living and fixed fibroblasts using time-lapse fluorescent imaging and confocal microscopy. Six of the seven new dyes were photostable and non-toxic in vitro at 10 μM concentration. In addition, they efficiently stained the cell membrane, showing diffuse and dotty localization within the cell at low concentrations (1.0 and 0.1 μM). Specifically, dye TC498 was localized in vesicular structures in both live and fixed cells and could be used as a suitable marker in co-staining studies with other commonly used fluorescent probes.

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Section: Chemistrymentioning

confidence: 99%

A Study on the Structure, Optical Properties and Cellular Localization of Novel 1,3-Benzothiazole-Substituted BODIPYs

Kirkilessi,

Arapatzi,

Reis

et al. 2023

Colorants

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“…The common method of preparing these benzazole derivatives involves the heterocyclization of either o-amino phenol or o-phenylene diamine with various aryl aldehydes as well as catalysts. [22][23][24][25][26][27][28][29][30][31][32][33] Although there are several methods for the synthesizing benzimidazole and benzoxazole derivatives, many of them associated with some limitations such as high temperature and strongly acidic conditions, low selectivity, tedious workup, prolonged reaction times, and low product yields. Also, a totally solvent-free and a deep eutectic solvent synthesis of the abovesaid compounds has been reported, but the use of high temperatures, toxic compounds such as urea, and so forth in these reactions is undesirable.…”

Section: Introductionmentioning

confidence: 99%

New phosphonium bromobismuthate as selective catalytic reagent in the heterocyclization reactions

Salmasi

Gholizadeh

Salimi

et al. 2023

Applied Organom Chemis

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A new hybrid phosphonium bromobismuthate compound was synthesized and characterized by 1H NMR, 13C NMR, 31P NMR, FT‐IR, differential scanning calorimetry (DSC) and single‐crystal X‐ray diffraction analysis. The crystal packing structures of title compound were stabilized by various intermolecular interactions especially of the type CH···Br hydrogen bonds between phosphonium cations and [Bi2Br9]3− anion. The relative contribution of various close contacts and 2D fingerprint plots of title compound and three analogous structures obtained from Cambridge Structural Database (CSD) were investigated by Hirshfeld surface analysis. Furthermore, the catalytic activity of title compound was investigated in heterocyclization reaction for the synthesis of significant and pharmacologically useful benzimidazole and benzoxazole derivatives. The results indicated that the yields of the product for aldehydes bearing p‐substituents and o‐substituents were higher than for m‐substituent ones. In addition to selectivity, simplicity of operation, waste minimization, ease of manipulation, short reaction time, excellent yield of product, and easy workup, this technique uses title compound as the catalyst, which is green, recyclable, soft, remarkably nontoxic, and easy to handle.

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“…Benzothiazole (Benzo[d]thiazol) is an important class of fused heterocyclic scaffold having broad range of pharmaceutical applications such as antimicrobial [17], anti-inflammatory [18], anticancer activities [19,20], neuroprotective [21], anti-helmintic [22], anticonvulsant [23], antiglutamate [24], antimalarial [25], antitubercular [26] and so on. Figure 1 represents a glimpse of drug molecules having benzothiazole as the core skeleton [27].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and Hirshfeld surface analysis of 2-aminobenzothiazol with 4-fluorobenzoic acid co-crystal

Banerjee

Sharma

et al. 2022

Eur J Chem

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The co-crystal of 2-aminobenzothiazol with 4-fluorobenzoic acid were synthesized and characterized by elemental analyses, spectral studies (FT-IR, NMR, HRMS) and single-crystal X-ray diffraction analysis. This compound co-crystallizes in the monoclinic space group P21/c (no. 14), a = 11.7869(14) Å, b = 4.0326(5) Å, c = 27.625(3) Å, β = 92.731(10)°, V = 1311.6(3) Å3, Z = 4, T = 293(2) K, μ(CuKα) = 2.345 mm-1, Dcalc = 1.470 g/cm3, 3568 reflections measured (7.508° ≤ 2Θ ≤ 134.202°), 2280 unique (Rint = 0.0262, Rsigma = 0.0413) which were used in all calculations. The final R1 was 0.0446 (I > 2σ(I)) and wR2 was 0.1274 (all data). The crystal structure is stabilized by elaborate system of N–H···O and O-H···O hydrogen bonds to form supramolecular structures. Furthermore, the 3D Hirshfeld surfaces and the associated 2D fingerprint plots have been analyzed for molecular interactions.

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Camphor sulfonic acid catalyzed a simple, facile, and general method for the synthesis of 2-arylbenzothiazoles, 2-arylbenzimidazoles, and 3H-spiro[benzo[d]thiazole-2,3′-indolin]-2′-ones at room temperature

Cited by 26 publications

References 122 publications

A Study on the Structure, Optical Properties and Cellular Localization of Novel 1,3-Benzothiazole-Substituted BODIPYs

A Study on the Structure, Optical Properties and Cellular Localization of Novel 1,3-Benzothiazole-Substituted BODIPYs

New phosphonium bromobismuthate as selective catalytic reagent in the heterocyclization reactions

Synthesis, characterization and Hirshfeld surface analysis of 2-aminobenzothiazol with 4-fluorobenzoic acid co-crystal

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