Efficient synthesis of new pyrano[2,3-d]pyrimidine-2,4-dione derivatives via a one-pot four-component reaction

Irani, Sharmin; Maghsoodlou, Malek Taher; Hazeri, Nourallah

doi:10.1007/s13738-017-1069-1

Cited by 8 publications

(1 citation statement)

References 48 publications

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“…Irani et al 133 used a four-component reaction of 1 with 11a , 92 , and 93 in ethanol as a solvent at room temperature to afford 94 ( Scheme 67 ). 1 with electron-releasing substituents gave higher isolated yield of 94 compared to electron-withdrawing substituents carrying aryl aldehyde 1 .…”

Section: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

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: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

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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Synthesis of novel thiazolo[3,2‐a]chromeno[4,3‐d]pyrimidine‐6(7H)‐ones by bioactive Fe₃O₄@gly@thiophen@Cu(NO₃)₂ as reusable magnetic nanocatalyst

Hosseinzadegan

Hazeri

Maghsoodlou

2020

Applied Organom Chemis

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In this study, new Fe3O4@gly@thiophen@Cu(NO3)2 magnetic nanoparticles were synthesized. The final product was used as an efficient and novel magnetic nanocatalyst for synthesizing new derivatives of thiazolo[3,2‐a] chromeno[4,3‐d]pyrimidine‐6(7H) in a short time and with higher efficiency. In the synthesis of Fe3O4@gly@thiophen@Cu(NO3)2 magnetic nanoparticles, the use of glycine proved an inexpensive and readily available coating for Fe3O4 than previously reported materials, and the structure was confirmed using scanning electron microscopy, transmission electron microscopy, X‐ray diffraction, energy‐dispersive x‐ray (EDX) spectroscopy, EDX mapping, Fourier‐transform infrared spectroscopy, thermogravimetric analysis/derivative thermogravimetry, and vibrating sample magnetometry. The biological properties of magnetic nanoparticles were evaluated, and they exhibited acceptable antifungal and antibacterial properties in terms of minimum inhibitory concentration, minimum fungicidal concentration, and minimum bactericidal concentration.

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An Organocatalytic Synthesis of Chiral Pyrano[2,3‐d]pyrimidines through [3+3] Annulation of 1,3‐Dimethyl‐barbituric Acid with 2‐(1‐Alkynyl)‐2‐alken‐1‐ones

et al. 2018

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An efficient enantioselective [3+3] annulation has been developed to synthesize chiral pyrano[2,3‐d]pyrimidines from 1,3‐dimethyl‐barbituric acid and 2‐(1‐alkynyl)‐2‐alken‐1‐ones. A thiourea‐tertiary amine bifunctional catalyst was synthesized and applied in the construction of the framework of chiral pyrano[2,3‐d]pyrimidines. The reaction proceeds smoothly on a broad range of substrates (18 examples) to produce the target products in moderate to good yields and enantioselectivities. Reduced temperature leads to an improvement of enantiomeric excesses. Steric hindrance plays an important role in the performance of the reaction.

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Efficient synthesis of new pyrano[2,3-d]pyrimidine-2,4-dione derivatives via a one-pot four-component reaction

Cited by 8 publications

References 48 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)

Synthesis of novel thiazolo[3,2‐a]chromeno[4,3‐d]pyrimidine‐6(7H)‐ones by bioactive Fe₃O₄@gly@thiophen@Cu(NO₃)₂ as reusable magnetic nanocatalyst

An Organocatalytic Synthesis of Chiral Pyrano[2,3‐d]pyrimidines through [3+3] Annulation of 1,3‐Dimethyl‐barbituric Acid with 2‐(1‐Alkynyl)‐2‐alken‐1‐ones

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Efficient synthesis of new pyrano[2,3-d]pyrimidine-2,4-dione derivatives via a one-pot four-component reaction

Cited by 8 publications

References 48 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)

Synthesis of novel thiazolo[3,2‐a]chromeno[4,3‐d]pyrimidine‐6(7H)‐ones by bioactive Fe3O4@gly@thiophen@Cu(NO3)2 as reusable magnetic nanocatalyst

An Organocatalytic Synthesis of Chiral Pyrano[2,3‐d]pyrimidines through [3+3] Annulation of 1,3‐Dimethyl‐barbituric Acid with 2‐(1‐Alkynyl)‐2‐alken‐1‐ones

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Synthesis of novel thiazolo[3,2‐a]chromeno[4,3‐d]pyrimidine‐6(7H)‐ones by bioactive Fe₃O₄@gly@thiophen@Cu(NO₃)₂ as reusable magnetic nanocatalyst