Synthesis of pyrano[2,3‐d]pyrimidines and pyrido[2,3‐d]pyrimidines in the magnetized deionized water based on UV–visible study

Bakherad, Mohammad; Bagherian, Ghadamali; Rezaeifard, Amin; Mosayebi, Fatemeh; Shokoohi, Behzad; Keivanloo, Ali

doi:10.1007/s13738-020-02073-z

Cited by 17 publications

(3 citation statements)

References 40 publications

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“…This protocol gave higher yield in shorter reaction time than entry 1 (Table 7). Bakherad et al 187 devised derivatives of 150 using magnetic deionized water at lower temperature gave comparatively higher yield in lower reaction time than entries 1 and 2 (Table 7). Jonnalagadda et al 188 developed novel analogue of 150 using two different methods, in which Method 1 involved the use of ethanol at 60 °C, giving only 20−59% yield and taking a higher reaction time than entries 2 and 3 (Table 7).…”

Section: Metal-catalyzed Synthesis Using the Electrolysis Methodmentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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The pyranopyrimidine core is a key precursor for medicinal and pharmaceutical industries due to its broader synthetic applications as well as its bioavailability. Among its four possible isomers, we found that 5H-pyrano[2,3-d]pyrimidine scaffolds have a wide range of applicability, and in recent years, they have been intensively investigated, but the development of the main core is found to be more challenging due to its structural existence. In this review article, we cover all of the synthetic pathways that are employed for the development of substituted 4-aryl-octahydropyrano/hexahydrofuro[2,3-d]pyrimidin-2-one (thiones) and 5-aryl-substituted pyrano[2,3-d]pyrimidindione (2-thiones) derivatives through a one-pot multicomponent reaction using diversified hybrid catalysts such as organocatalysts, metal catalysts, ionic liquid catalysts, nanocatalysts, green solvents, catalyst-/solvent-free conditions, and miscellaneous catalysts as well as the mechanism and recyclability of the catalysts. This review mainly focuses on the application of hybrid catalysts (from 1992 to 2022) for the synthesis of 5H-pyrano[2,3-d]pyrimidine scaffolds. This review will definitely attract the world’s leading researchers to utilize broader catalytic applications for the development of lead molecules.

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Section: Metal-catalyzed Synthesis Using the Electrolysis Methodmentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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“…A technique that is environmentally friendly for the synthesis of pyrano[2,3-d] pyrimidines 4 was reported by Bakherad and colleagues in 2020. [34] They used magnetized deionized water (MDW) as a green solvent without requiring a catalyst. The reactions were fast and yielded high to excellent products (Scheme 3).…”

Section: Catalyst-free Synthesis Of Pyrano[23-d]pyrimidine Compoundsmentioning

confidence: 99%

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

Rezaeifard,

Bakherad,

Navidpour

et al. 2024

ChemistrySelect

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Due to their extensive applications in pharmaceuticals and natural substances, organic synthesis and heterocyclic compounds have been at the forefront of research for many years. Pyrimidine is one of the heterocyclic compounds that have various derivatives with promising biological and pharmacological properties. This review article covers the synthesis and biological effects of pyrimidine derivatives, such as pyrano[2,3‐d]pyrimidines, pyrido[2,3‐d]pyrimidines, and furo[2,3‐d]pyrimidines. The compounds discussed in this review have a wide range of biological activities. Recent advances in green chemistry have led to the development of eco‐friendly synthetic methods for producing these bioactive heterocycles. This review aims to present various synthetic methods and biological effects of these compounds and provide new opportunities for organic chemists to develop potent nitrogen‐ and oxygen‐containing heterocycles for future applications. The review highlights examples of successful syntheses and applications of pyrimidine derivatives in the fields of antibacterial, antifungal, anticancer, enzyme inhibition, and antiviral research.

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“…The role of magnetized water involved the activation of the carbonyl group of dimethyl barbituric acid, which enabled the enolization and activate the aldehydic group of aryl aldehydes for condensation with malononitrile, and activation of nitrile groups of the generated intermediates by interaction with nitrogen atoms. 46 Otherwise, Tabassum et al 47 have developed identical reaction sequences for the synthesis of bicyclic pyranopyrimidines with remarkable yields (90-96%) under catalytic conditions using nano ZnO@PEG. Thus, treatment of aryl aldehydes with malononitrile or methyl cyanoacetate, and barbituric acid through multicomponent one-pot reactions in ethanol at 25 C gave the desired products 5 (Scheme 3).…”

Section: Synthesis Of Bicyclic Systemsmentioning

confidence: 99%

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

2022

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Synthesis of pyrano[2,3‐d]pyrimidines and pyrido[2,3‐d]pyrimidines in the magnetized deionized water based on UV–visible study

Cited by 17 publications

References 40 publications

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

Recent advancements in the multicomponent synthesis of heterocycles integrated with a pyrano[2,3-d]pyrimidine core

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