Efficient sodium bisulfite-catalyzed synthesis of benzothiazoles and their potential as ureases inhibitors

Araújo, Débora P.; Morais, Vinicius Stefano Santos; Fátima, Ângelo de; Modolo, Luzia V.

doi:10.1039/c5ra01081k

Cited by 24 publications

(6 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…IrCl 3 ⋅ nH 2 O, 2‐(1H‐imidazol‐2‐yl)pyridine (piz) and 2‐(pyridin‐2‐yl)‐1H‐benzoimidazole (pbiz) were purchased from Bide Pharmatech Co., Ltd. The R‐pbt liagnds 2‐(4‐methoxyphenyl)benzo[d]thiazole (CH 3 Opbt), [50] 2‐(4‐(trifluoromethyl)phenyl)benzo[d]thiazole (CF 3 pbt) [51] and 2‐(4‐fluorophenyl)benzo[d]thiazole (Fpbt) [52] were prepared according to the literature procedures, and the 1 H NMR spectroscopies have been tested for verifying the purity.…”

Section: Methodsmentioning

confidence: 99%

A series of 2‐phenylbenzothiazole‐based iridium complexes with N‐H derivatives: synthesis, photophysics, DFT calculations and a preliminary exploration in fluoride ions sensing

Chen,

Zhou,

Xiang

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

A series of new pbt‐based Ir(III) complexes containing N−H derivatives ancillary ligands (piz/pbiz) were designed and synthesized rationally, naming [(CH3Opbt)2Ir(piz)][PF6] (Ir1), [(CF3pbt)2Ir(piz)][PF6] (Ir2), [(Fpbt)2Ir(piz)][PF6] (Ir3), [(CH3Opbt)2Ir(pbiz)][PF6] (Ir4), [(CF3pbt)2Ir(pbiz)][PF6] (Ir5) and [(Fpbt)2Ir(pbiz)][PF6] (Ir6) (where pbt=2‐phenylbenzothiazole, piz=2‐(1H‐imidazol‐2‐yl)pyridine, and pbiz=2‐(pyridin‐2‐yl)‐1H‐benzoimidazole). Combined with photophysical properties and theoretical calculations, their structure‐property relationships were systematically researched. These iridium(III) complexes are phosphorescent in the green and yellow‐green region with quantum yields of 14.1–28.7 % and lifetimes of 0.35–0.88 μs. Considering the relatively high quantum yield and imidazole group on ancillary ligands, [(CF3pbt)2Ir(pbiz)][PF6] (Ir5) was preliminary explored as the phosphorescent sensor toward F− ions. The results showed that the addition of fluoride ions to complex Ir5 in dichloromethane solution induced a red shift of the emission color, along with an enhancement in the luminescent intensity. Theoretical calculations were carried out to understand the mechanism, and the results reveal that the hydrogen bonding interaction of N−H bond with F− influence the electron transfer processes of the lowest energy absorption and emission, leading to a significant change in the photophysical properties.

show abstract

Section: Methodsmentioning

confidence: 99%

A series of 2‐phenylbenzothiazole‐based iridium complexes with N‐H derivatives: synthesis, photophysics, DFT calculations and a preliminary exploration in fluoride ions sensing

Chen,

Zhou,

Xiang

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Benzoic acid, o ‐hydroxyaniline, 2‐aminothiophenol, and IrCl 3 ‧nH 2 O were purchased from Energy Chemical. The ligands, potassium bis(diphenylthiophosphoryl)amide (S‐tpipK) [32], 2‐phenylbenzo[d]oxazole (bo) [51], 2‐phenylbenzo[d]thiazole (bt) [52], and 2‐(thiophen‐2‐yl) benzo[d]thiazole (thbt) [53] were synthesized according to the literature procedure. All other reagents were used without further purification unless otherwise stated.…”

Section: Methodsmentioning

confidence: 99%

Influential effect of C^N ligands containing O, S, and Se heteroatoms in the color tuning of four phosphorescent Ir(III) complexes

Chen,

Ma,

et al. 2024

J Chinese Chemical Soc

View full text Add to dashboard Cite

A group of new iridium(III) complexes were rationally designed and synthesized with 2‐phenylbenzo[d]oxazole (bo), 2‐phenylbenzo[d]thiazole (bt), 2‐(thiophen‐2‐yl)benzo[d]thiazole (thbt), and 2‐(selenophen‐2‐yl)benzo[d]thiazole (sebt) as C^N ligands and bis(diphenylthiophosphoryl)amide (S‐tpip) as ancillary ligand. They are phosphorescent in a wide region of green to red with short lifetimes around 0.31–0.98 μs and quantum yields up to 64.7%. The detailed photophysical properties were investigated by experiment and further supported by density functional theory (DFT) calculation. These research results show that the spectroscopic properties are tuned by the replacement between oxygen, sulfur, and selenium or the change in aromatic ring. It has been demonstrated that the lowest energy‐level absorption and emission are dominated apparently by C^N ligands, and are ascribed to metal‐to‐ligand charge transfer (MLCT) and intra‐ligand charge transfer (ILCT) characters.

show abstract

“…[385][386][387] Previous methods for synthesizing these compounds have involved the use of metal catalysts such as Pd (Scheme 41 (a) and (c)), Ru (Scheme 41 (b) and (d)) or combinations of PhCl/DMSO (Scheme 41 (e)), xylene (Scheme 41 (f)), or DMA (Scheme 41 (g)). [388][389][390][391][392][393][394] Some metal-free approaches have also been explored by malakar and group for the similar transformations. [395,396] But most of the discussed synthetic routes required expensive and complex starting materials.…”

Section: Cà N Bond Formationmentioning

confidence: 99%

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis of the use of iodine and DMSO in various synthetic routes for the preparation of valuable targets are presented. These methods reduce the acceptance on expensive additives and reagents, and offer a more sustainable solution for the synthesis of these important chemical scaffolds.

show abstract

Efficient sodium bisulfite-catalyzed synthesis of benzothiazoles and their potential as ureases inhibitors

Abstract: In this work we report the successful use of sodium bisulfite as catalyst for the synthesis of 19 benzothiazoles (BZTs) under microwave irradiation with yields from 80% to 100%.

Cited by 24 publications

References 68 publications

A series of 2‐phenylbenzothiazole‐based iridium complexes with N‐H derivatives: synthesis, photophysics, DFT calculations and a preliminary exploration in fluoride ions sensing

A series of 2‐phenylbenzothiazole‐based iridium complexes with N‐H derivatives: synthesis, photophysics, DFT calculations and a preliminary exploration in fluoride ions sensing

Influential effect of C^N ligands containing O, S, and Se heteroatoms in the color tuning of four phosphorescent Ir(III) complexes

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Contact Info

Product

Resources

About