Synthesis of substituted pyrimidine using <scp>ZnFe<sub>2</sub>O<sub>4</sub></scp> nanocatalyst via one pot multi‐component reaction ultrasonic irradiation

Chavan, Pravin; Bangale, S. V.; Pansare, Dattatraya N.; Shelke, Rohini N.; Jadhav, Shivaji; Tupare, Shrikrushna; Kamble, Dhanraj; Rai, Megha

doi:10.1002/jhet.4048

Cited by 12 publications

(7 citation statements)

References 36 publications

(29 reference statements)

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“…Other cyclic and noncyclic active methylene compounds can be used in multicomponent reactions with 2‐aminobenzimidazole and aldehydes under green conditions. For example, Chavan and co‐authors [237] described the synthesis of 2‐amino‐4‐substituted 1,4‐dihydrobenzo[4,5]imidazo[1,2‐ a ]pyrimidine‐3‐carbonitriles 154 via one‐pot three‐component condensation reaction of benzimidazole 135 , malononitrile 153 and aromatic aldehyde 32 using heterogeneous ZnFe 2 O 4 nanoparticles as catalyst at 70 °C under ultrasonic irradiation (Scheme 60).…”

Section: Green Chemistry and Non‐classical Activation Methodsmentioning

confidence: 99%

“…A sequential one-pot four component procedure (Scheme 59) of an amine 150, 2,2,6-trimethyl-4H-1,3-dioxin-4-one 151, an aldehyde 32 and 2-aminobenzimidazole 135 without the use of a catalyst for the synthesis of benzo [4,5]imidazo[1,2-a]-pyrimidine-3-carboxamides 152 was developed by Shaabani et al [236] Other cyclic and noncyclic active methylene compounds can be used in multicomponent reactions with 2-aminobenzimidazole and aldehydes under green conditions. For example, Chavan and co-authors [237] Multicomponent reaction of the same starting materials catalyzed by starch functionalized magnetite nanoparticles (Fe 3 O 4 ) in aqueous medium at room temperature under ultrasonic irradiation was studied in other article. [207] Furthermore, Joshi and Bhatt [238] reported ultrasonic-assisted similar three-component reaction of 2-chloroquinoline-3-carbaldehyde with 2-aminobenzimidazole and malononitrile in the presence of ammonium acetate as catalyst in ethanol.…”

Section: Reactions Of 2-aminoimidazole and 2-aminobenzimidazolementioning

confidence: 99%

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Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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Dihydroazolopyrimidines are an important class of heterocycles that are isosteric to natural purines and are therefore of great interest primarily as drug‐like molecules. In contrast to the heteroaromatic analogs, synthetic approaches to these compounds were developed much later, and their chemical properties and biological activity have not been studied in detail until recently. In the review, different ways to build dihydroazolopyrimidine systems from different building blocks are described – via the initial formation of a partially hydrogenated pyrimidine ring or an azole ring, as well as a one‐pot assembly of azole and azine fragments. Special attention is given to modern approaches: multicomponent reactions, green chemistry, and the use of non‐classical activation methods. Information on the chemical properties of dihydroazolopyrimidines and the prospects for their use in the design of drugs of various profiles are also summarized in this review.

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Section: Green Chemistry and Non‐classical Activation Methodsmentioning

confidence: 99%

Section: Reactions Of 2-aminoimidazole and 2-aminobenzimidazolementioning

confidence: 99%

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Desenko,

Gorobets,

Lipson

et al. 2023

The Chemical Record

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“…Chavan et al [39] described an extremely effective one-pot three The fast reaction time, ease of handling, simplicity, efficiency, high yield, and recyclable catalyst are all important features of this synthetic technique (Scheme 31).…”

Section: Chemistryselectmentioning

confidence: 99%

“…Scheme 51. Under ultrasonic irradiation, tetrasubstituted imidazole derivatives are synthesised "reproduced with permission from[39], copyrights 2020, Elsevier." Scheme 52.…”

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confidence: 99%

Reusable Nano Catalysed Synthesis of Heterocycles: An Overview

Sonawane¹,

Deore²,

Chavan

2022

ChemistrySelect

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The field of reusable nano‐catalysts has grown rapidly over the last decade. Recently, transition metal catalysed organic reactions have attracted considerable interest from the pharmaceutical and organic chemistry fields. Synthetic procedures based on such heterogeneous nanocatalysts are easier, less expensive, non‐toxic, and eco‐friendly, producing only the most desirable products in higher yields and allowing for easy catalyst separation. Heterogeneous nano‐catalysts were highly preferred over homogeneous catalysts for the synthesis of heterocyclic compounds due to their effective separation processes for both products and catalysts. According to recent studies, nanoparticles (NPs) are commonly used as a heterogeneous catalyst in the production of heterocyclic compounds. Heterogeneous catalysts are widely used in a variety of organic reactions due to their high surface‐to‐volume ratio. Most importantly, after the reaction is complete, easy magnetic separation of the catalyst minimises the requirement for catalyst filtration. Additionally, magnetic NPs, particularly supported magnetic nanocatalysts, have garnered considerable interest in both academic and industrial research due to their effectiveness as alternatives to traditional materials, their ease of separation via an external magnet, and their high degree of chemical stability in a variety of organic and inorganic solvents. To reach its depth, this review is focused on the most recent examples, their preparation, synthetic strategies and recycling studies of highly excited catalytic systems used for the synthesis of heterocyclic compounds.

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“…Owing to their importance, the development of benzo [4,5]imidazo [1,2-a]pyrimidines have been reported by means of simple condensation of 2-aminobenzimidazole, an array of aromatic aldehydes, and a couple of C-H activated acids using a number of catalysts such as 1,4-piperazinium hydrogen sulfate ([H-pi]HSO 4 ) [10], ZnFe 2 O 4 NPs [11], p-TSA [12], nano-Ag-TiO 2 [13], [(4-SO 3 H)BMIM]HSO 4 [14], MMT-HClO 4 [15], Iron oxide@PMO-ICS-PrSO 3 H [16], RHA-[pmim]HSO 4 [17], Thiamine hydrochloride (VB 1 ) [18], L-proline [19], and [bmim + ][BF 4 À ] [20].…”

Section: Introductionmentioning

confidence: 99%

Microwave‐assisted synthesis of benzo[4,5]imidazo[1,2‐a]pyrimidines and pyrano[4,3‐b]pyrans catalyzed by L‐glutamine functionalized magnetic nanoparticles in water:ethanol mixture

Thongni,

Nongkhlaw,

Pandya

et al. 2024

Journal of Heterocyclic Chem

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In this work, we report an effective, one‐pot syntheses of benzo[4,5]imidazo[1,2‐a]pyrimidine and pyrano[4,3‐b]pyran derivatives using L‐glutamine functionalized nanoparticles (Fe3O4@SiO2@L‐glutamine NPs) under microwave irradiation. The organo‐nanocatalyst underwent characterization through diverse techniques, including FT‐IR, p‐XRD, SEM, TEM, EDX, XPS, TGA, and VSM. Microwave irradiation and multicomponent reactions synergistically yield excellent product yields (≈80%–95%) in shorter reaction times (≈6–15 min) with a broader substrate scope. The organo‐nanocatalyst displays notable catalytic efficacy, evidenced by high turnover numbers (TON) and turnover frequencies (TOF) across syntheses. This innovative protocol showcases exceptional efficiency, cost‐effectiveness, and environmental friendliness, with advantages like minimal reaction conditions, easy catalytic recovery, recyclability, operational simplicity, and the use of eco‐friendly solvents.

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Synthesis of substituted pyrimidine using ZnFe₂O₄ nanocatalyst via one pot multi‐component reaction ultrasonic irradiation

Cited by 12 publications

References 36 publications

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Reusable Nano Catalysed Synthesis of Heterocycles: An Overview

Microwave‐assisted synthesis of benzo[4,5]imidazo[1,2‐a]pyrimidines and pyrano[4,3‐b]pyrans catalyzed by L‐glutamine functionalized magnetic nanoparticles in water:ethanol mixture

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Synthesis of substituted pyrimidine using ZnFe2O4 nanocatalyst via one pot multi‐component reaction ultrasonic irradiation

Cited by 12 publications

References 36 publications

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Dihydroazolopyrimidines: Past, Present and Perspectives in Synthesis, Green Chemistry and Drug Discovery

Reusable Nano Catalysed Synthesis of Heterocycles: An Overview

Microwave‐assisted synthesis of benzo[4,5]imidazo[1,2‐a]pyrimidines and pyrano[4,3‐b]pyrans catalyzed by L‐glutamine functionalized magnetic nanoparticles in water:ethanol mixture

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Synthesis of substituted pyrimidine using ZnFe₂O₄ nanocatalyst via one pot multi‐component reaction ultrasonic irradiation