Lanthanum (III) nitrate hexahydrate catalyzed one-pot synthesis of 2-arylbenzothiazoles under mild reaction conditions

Shaikh, Kabeer A.; Chaudhar, Uddhav N

doi:10.25135/acg.oc.29.17.08.044

Cited by 8 publications

(2 citation statements)

References 34 publications

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“…There are more than 100 Lewis acids catalysts that have been reported to promote the condensation of 2-aminothiophenols 22 with aldehydes 23, exemplified in Table 2 with 2-aminothiophenol and benzaldehyde, such as I 2 , 22 (Cu(II)-glycerol/MCM-41, 23 TiO 2 /Al 2 O 3 , 24 YCl 3 , 25 ZnO, 26 Fe-Cl 3 , 27 etc. [28][29][30][31][32][33][34] For instance, in 2019, Tan and co-workers developed a novel catalytic route for the synthesis of 2-arylbenzothiazoles 24 via condensation of 2-aminothiophenols 22 with aldehydes 23 via I 2 /di-tert-butyl peroxide (DTBP) promoted one-pot tandem cyclization and oxidation sequence (Table 2, entry 1). 22 In 2019, Ding, Luo and co-workers group also reported a base-promoted one-pot process for the synthesis of bioactive 2-[2-(difluoromethoxy)aryl]benzothiazole derivatives.…”

Section: Classic Condensation Of 2-aminothiophenolsmentioning

confidence: 99%

Recent Advances in the Synthesis and Applications of 2-Arylbenzothiazoles

et al. 2020

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This review firstly covers the applications of 2-arylbenzothiazoles as amyloid imaging agents, antitumor agents, and organic luminescent materials. Then we review the recent advances in the synthesis of 2-arylbenzothiazole derivatives. On the one hand, we introduce the approaches for construction of the 2-arylbenzothiazole core, including the following categories: (i) classic condensation of 2-aminothiophenols, (ii) direct arylation of benzothiazoles, (iii) intramolecular cyclization of thiobenzanilides, and (iv) tandem cyclization of anilines/ nitroarenes with elemental sulfur or sulfides. On the other hand, the transition-metal-catalyzed direct C–H functionalizations of 2-arylbenzothiazoles are also involved in this review.1 Introduction2 Applications of 2-Arylbenzothiazoles3 Construction of the 2-Arylbenzothiazole Core4 Synthesis 2-Arylbenzothiazoles via Direct C–H Functionalization5 Conclusion

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Section: Classic Condensation Of 2-aminothiophenolsmentioning

confidence: 99%

Recent Advances in the Synthesis and Applications of 2-Arylbenzothiazoles

et al. 2020

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“… 48 And the two probes were easily obtained based on the condensation reaction of 2-aminothiophenol and aromatic aldehydes in the presence of catalytic amount of lanthanum( iii ) nitrate hexahydrate in a considerable yield under mild conditions. 49 The difference of the probes in structure is that BS1 possesses a reactive electron withdrawing diphenyl phosphonate unit while BS2 bears a pinacol boronic ester group for monitoring ONOO − . Both probes showed excellent sensitivity and rapid response toward ONOO − in comparison with the previously reported ONOO − probes (Table S1 † ).…”

Section: Introductionmentioning

confidence: 99%

Highly sensitive benzothiazole-based chemosensors for detection and bioimaging of peroxynitrite in living cells

Kong

Wang

et al. 2022

RSC Adv.

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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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Lanthanum (III) nitrate hexahydrate catalyzed one-pot synthesis of 2-arylbenzothiazoles under mild reaction conditions

Cited by 8 publications

References 34 publications

Recent Advances in the Synthesis and Applications of 2-Arylbenzothiazoles

Recent Advances in the Synthesis and Applications of 2-Arylbenzothiazoles

Highly sensitive benzothiazole-based chemosensors for detection and bioimaging of peroxynitrite in living cells

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

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