Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by silica sulfuric acid

Chen, Guo Feng; Zhang, Li Yan; Jia, Hui Ming; Chen, Bao Hua; Li, Ji Tai; Wang, Shu Xiang; Bai, Guo Yi

doi:10.1007/s11164-012-0739-y

Cited by 13 publications

(5 citation statements)

References 46 publications

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“…This mechanism has potential application in the suppression of tumor progression in breast cancer cells [13][14][15][16][17]. The synthesis of the title compound has been recently improved by using several catalysts such as LiBr [18], ZnO [19] and CdS [20], silica [21], nanoparticles, clays [22,23], and transition metals [24,25]. The number of synthetic methods reflects the importance of this compound.…”

Section: Introductionmentioning

confidence: 99%

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

et al. 2017

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Abstract:Benzothiazoles are a set of molecules with a broad spectrum of biological applications. In particular, 2-(4-hydroxy-3-methoxyphenyl)-benzothiazole is a potential breast cancer cell suppressor whose mechanism of action has been previously reported. In the present work, the title compound was synthesized, crystallized, and its biological activity on HeLa cells was evaluated. Its molecular structure was compared to that obtained by molecular modeling. Theoretical calculations suggest that the syn-rotamer is the most stable form and correlates very well with crystallographic data. The crystal structure adopts a helical arrangement formed through O13-H13···N3 intermolecular hydrogen bonding that propagates in the (14 -1 -3) plane. These results suggest that the title compound has the capacity to interleave into DNA and better explain its biological effects related to the increased CHIP expression through AhR recruitment. Finally, the biological experiments indicate that the title compound has the capacity to decrease the viability of HeLa cells with an IC 50 = 2.86 µM.

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Section: Introductionmentioning

confidence: 99%

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

et al. 2017

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“…Chen et al [210] used silica-supported sulfuric acid as a stable solid acid catalyst in the one-pot synthesis of 2-substituted benzothiazoles (19). Initially, the reaction was explored with different solvents and varying catalyst amounts in order to establish the optimized reaction conditions.…”

Section: Silica-supported Reagentsmentioning

confidence: 99%

“…Silica-supported H 2 SO 4 mediated synthesis of 2-substituted benzothiazoles. [210] Scheme 28. Silica-supported nano-CuO mediated synthesis of 2-substituted benzothiazoles.…”

Section: Silica-supported Reagentsmentioning

confidence: 99%

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Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

et al. 2021

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Benzothiazole and its derivatives have been manifested as an optimistic scaffold due to their immense biological importance. Several methodologies have been reported as modifications after the first report of 2-substituted benzothiazole. Among them, many involve a shift from the conventional synthetic approach by utilizing different catalytic systems. Moreover, synthetic methodologies focused on improvements in terms of product yield, reaction duration, use of environmentally benign conditions and simplified workup procedures predominate among the recently developed approaches. Solid-phase organic synthesis received considerable attention with the pioneering findings of Merrifield's solid-phase peptide synthesis in 1963. A diverse range of organic, inorganic and organic-inorganic substances have been utilized as polymeric solid supports in various catalytic applications. The recyclability and reusability of the immobilized catalysts over consecutive cycles establish them as an attractive alternative over conventional catalytic systems from the environment as well as industrial perspective. The present review summarizes the recent developments in the environmentally benign synthesis of benzothiazole derivatives using supported reagents. Different solid supports along with their catalytic application, mechanistic perspective and substrate tolerance have been discussed comprehensively.

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“…The most used method for synthesizing 2-substituted benzothiazoles involves the direct condensation of 2-aminothiophenols with substituted aldehydes. In recent years, there has been a growing interest in developing eco-friendly strategies to make this method more sustainable. − Despite efforts to improve this method, the existing approaches still possess certain limitations such as the utilization of acids, bases, toxic organic solvents, or the involvement of expensive transition metal catalysts with ligands, prolonged reaction times, high temperatures, reduced yields, lack of large-scale transposition, generation of waste products, and the requirement of complex purification steps and techniques.…”

Section: Introductionmentioning

confidence: 99%

Thiourea as Bifunctional Hydrogen Bond Donor and Brønsted Base Catalyst for Green One-Pot Synthesis of 2-Aryl/Heteroaryl/Styryl Benzothiazoles in the Aqueous Medium under Ultrasound Irradiation

Saini,

Manju,

Raigar

et al. 2024

ACS Omega

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A green organocatalysis cascade strategy using thiourea in catalytic amounts as both a hydrogen bond donor and a Brønsted base bifunctional catalyst was utilized to synthesize a series of 2-aryl/heteroaryl/styryl benzothiazole derivatives. This strategy involved an ultrasound-irradiated one-pot two-component reaction between substituted aldehydes and 2-amino thiophenols in an aqueous medium at 60 °C, using air as an oxidant. At the gram-scale, this protocol yielded 87% of the desired product, making it suitable for production at a larger scale. This green and mild protocol offers excellent yields, cost-effectiveness, atom economy, step economy, and a simple operation that does not require extra purification steps. Furthermore, the catalyst is easily recoverable and can be used for up to five cycles without a significant loss of any activity.

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Eco-friendly synthesis of 2-substituted benzothiazoles catalyzed by silica sulfuric acid

Cited by 13 publications

References 46 publications

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

Helical Arrangement of 2-(4-hydroxy-3-methoxyphenyl)-Benzothiazole in Crystal Formation and Biological Evaluation on HeLa Cells

Solid‐Supported Materials‐Based Synthesis of 2‐Substituted Benzothiazoles: Recent Developments and Sanguine Future

Thiourea as Bifunctional Hydrogen Bond Donor and Brønsted Base Catalyst for Green One-Pot Synthesis of 2-Aryl/Heteroaryl/Styryl Benzothiazoles in the Aqueous Medium under Ultrasound Irradiation

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