Green synthesis and characterisation of novel [1,3,4]thiadiazolo/benzo[4,5]thiazolo[3,2-<i>a</i>]pyrimidines <i>via</i> multicomponent reaction using vanadium oxide loaded on fluorapatite as a robust and sustainable catalyst

Kerru, Nagaraju; Gummidi, Lalitha; Bhaskaruni, Sandeep V. H. S.; Maddila, Suresh; Jonnalagadda, Sreekantha B.

doi:10.1039/d0ra02298e

Cited by 31 publications

(14 citation statements)

References 51 publications

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“…TEM and SEM) of the prepared [SnS-NPs@AC] specified that the nanoparticles had a homogeneously spherical morphology and were in the range of (40-90 nm) and (30-70 nm), respectively, which was in agreement with the PXRD (64 nm) outcomes. The multicomponent reaction of 3-methyl-pyrazolinone (8), various aldehydes (24), malononitrile (3) and catalyst in ethanol solvent led to the target compounds at 80 • C for 25 min reaction time with excellent yields (85-91%) (Scheme 7). The nanocatalyst performed eight cycles with sustained activity.…”

Section: Single Metal-containing Catalystsmentioning

confidence: 99%

“…On the other hand, multicomponent reactions (MCRs) have steadily gained significance in synthetic organic chemistry [ 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. MCRs offer many benefits—e.g., greater yields, high atom efficiency, reduced reaction time, high convergence, minimisation of purification requirements and waste generation—compared to multiple-step syntheses [ 20 , 21 , 22 , 23 , 24 , 25 ]. Typically, multi-step procedures require the purification of reaction products in each step and demand appropriate solvents and reagents.…”

Section: Introductionmentioning

confidence: 99%

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Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review

et al. 2021

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Heterogeneous catalysis plays a crucial role in many chemical processes, including advanced organic preparations and the design and synthesis of new organic moieties. Efficient and sustainable catalysts are vital to ecological and fiscal viability. This is why green multicomponent reaction (MCR) approaches have gained prominence. Owing to a broad range of pharmacological applications, pyranopyrazole syntheses (through the one-pot strategy, employing sustainable heterogeneous catalysts) have received immense attention. This review aimed to emphasise recent developments in synthesising nitrogen-based fused heterocyclic ring frameworks, exploring diverse recyclable catalysts. The article focused on the synthetic protocols used between 2010 and 2020 using different single, bi- and tri-metallic materials and nanocomposites as reusable catalysts. This review designated the catalysts’ efficacy and activity in product yields, reaction time, and reusability. The MCR green methodologies (in conjunction with recyclable catalyst materials) proved eco-friendly and ideal, with a broad scope that could feasibly lead to advancements in organic synthesis.

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Section: Single Metal-containing Catalystsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review

et al. 2021

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“…Nitrogen-based heterocyclic skeletons have prominence in synthetic organic chemistry because of their valuable biological applications (Kerru et al, 2019c;Kerru et al, 2020k;Kerru et al, 2020l;Rao et al, 2021b;Kumar et al, 2021). Among the several nitrogen heterocycles, dihydropyridines have received enormous attention due to their wide range of therapeutic properties.…”

Section: Introductionmentioning

confidence: 99%

Recent Progresses in the Multicomponent Synthesis of Dihydropyridines by Applying Sustainable Catalysts Under Green Conditions

et al. 2021

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The synthesis of dihydropyridines, valuable molecules with diverse therapeutic properties, using eco-friendly heterogeneous catalysts as a green alternative received significant consideration. By selecting appropriate precursors, these compounds can be readily modified to induce the desired properties in the target product. This review focused on synthesising diverse dihydropyridine derivatives in single-pot reactions using magnetic, silica, and zirconium-based heterogeneous catalytic systems. The monograph describes preparation techniques for various catalyst materials in detail. It covers facile and benign magnetic, silica, zirconium-based, and ionic liquid catalysts, exhibiting significant efficacy and consistently facilitating excellent yields in short reaction times and in a cost-effective way. Most of the designated protocols employ Hantzsch reactions involving substituted aldehydes, active methylene compounds, and ammonium acetate. These reactions presumably follow Knoevenagel condensation followed by Michael addition and intra-molecular cyclisation. The multicomponent one-pot protocols using green catalysts and solvents have admirably increased the product selectivity and yields while minimising the reaction time. These sustainable catalyst materials retain their viability for several cycles reducing the expenditure are eco-friendly.

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“…Most of the compounds exhibited potent cytotoxic activity against tumor cell line A549 (non-small cell lung cancer cell line) [23] using sulforhodamine B (SRB) standard method [24]. Recently, Nagaraju and co-workers reported green synthesis [25] and characterization of thiadiazolo [3,2-a]pyrimidines via the multi-component reaction between chosen substrates of 2-aminothiadiazoles, aldehydes and active methylene compounds in ethanol solvent at room temperature using vanadium oxide loaded on uorapatite as a robust and sustainable catalyst. Recently, 7-oxo-7H- [1,3,4]thiadiazolo [3,2-a]pyrimidine-5-carboxylate derivatives were conveniently synthesized under mild condition through regioselective cycloaddition reactions [26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Screening of New Thiadiazolopyrimidine-based Polycyclic Compounds

Alqahtani

2021

Preprint

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New tri- and tetra-cyclic compounds based on the thiadiazolopyrimidine ring system were prepared and their antimicrobial activity were estimated. The achieved results evidenced that pyrano-thiadiazolopyrimidine compounds 8a-b and 9a-b have substantial efficiencies toward the two strains of Gram-positive bacteria (S. aureus and B. cereus). While tetracyclic derivatives pyrazolopyrimido-thiadiazolopyrimidine derivatives 16a-b and 17a-b displayed prominent efficiencies toward the two strains of Gram-negative bacteria (E. coli and P. aeruginosa). In addition, compounds 8a-b and 9a-b presented good efficacy toward C. albicans. The activity of antiquorum-sensing (anti-QS) inhibition of the new synthesized thiadiazolopyrimidine-based compounds was tested toward C. violaceum, where derivatives 16a-b, 17a-b, 8b and 9a displayed satisfactory activity. Cytotoxic activity of the same derivatives was screened toward various cancer cell lines (MCF-7, PC3, Hep-2 and HepG2) and standard normal fibroblast cell (WI38) by utilizing the MTT assay. The pyrazolopyrimido-thiadiazolopyrimidine derivatives 16a, 16b, 17a and 17b recorded potent cytotoxic efficacy against MCF-7 cells with IC50 values ranging from 5.69 to 9.36 µM. Also, the endorsed structural activity relationship (SAR) for the inspected thiadiazolopyrimidine derivatives provided an awareness concerning the chemical structure connected to anticancer efficiency. In silico docking studies were implemented toward silence hormone signaling in breast (PDB Code-5NQR). The results are consistent and supportive to the cytotoxic activity.

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Green synthesis and characterisation of novel [1,3,4]thiadiazolo/benzo[4,5]thiazolo[3,2-a]pyrimidines via multicomponent reaction using vanadium oxide loaded on fluorapatite as a robust and sustainable catalyst

Abstract: We synthesized material with different loading of vanadia on fluorapatite (V2O5/FAp), and excellent activity was showed for the synthesis of pyrimidine derivatives (90–97%) in ethanol medium for short reaction time.

Cited by 31 publications

References 51 publications

Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review

Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review

Recent Progresses in the Multicomponent Synthesis of Dihydropyridines by Applying Sustainable Catalysts Under Green Conditions

Synthesis and Biological Screening of New Thiadiazolopyrimidine-based Polycyclic Compounds

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