A One Pot Synthesis of 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-D] pyrimidin-2, 4-diones (or 2-thioxo-4-ones)

Rahman, Md. Shahidur; Ahmed, S.M. Zabed; Siddiki, Sma Hakim; Halim, Ershad; Akhter, Khaleda; Ahmed, Monzur Morshed; Romman, Ukr

doi:10.3329/dujs.v61i2.17065

Cited by 4 publications

(2 citation statements)

References 12 publications

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“…Rahman et al 113 have also synthesized other analogues of 70 by reacting arylidene-acetophenone 68 (5 mmol) with 11 (5 mmol) in 15 mL of AcOH with P 2 O 5 (2 g) under reflux condition for 6–8.5 h at 135–140 °C to get the intermediate 68b and 68c which was then undergo cyclization to get 70 ( Scheme 52 ). After reaction completion, the pure product was obtained via recrystallization using R-spirit.…”

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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“…With this background, in continuation to our works (Ahmed et al, 2006;Ahmed et al, 2011;Ullah et al, 2012;Rahman et al, 2013;Akhter et al, 2016) on the synthesis of barbituric acid and thio-barbituric acid derivatives, we report herein syntheses of 5, 7-diaryl-1,5-dihydro -pyrano [2, 3-d] pyrimidin-2, 4-diones (3b, 3d & 3e) and 5, 7-diaryl-2-thioxo -1, 2, 3, 5-tetrahydro-pyrano [2, 3-d] pyrimidin -4-ones) (3a, 3c, 3f & 3g) by selecting a number of arylideneacetophenones (2a-d) as the a , ß-unsaturated carbonyl system having different substituents on the aromatic *Corresponding author e-mail: kawsariakhter@yahoo.com rings for reaction with barbituric acid or thiobarbituric acid (1) as the active methylene component in presence of glacial acetic acid and phosphorus pentoxide (Scheme 1). The compounds 3a-g do not seem to be available in the literature.…”

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confidence: 99%

One step cyclocondensation of (thio) barbituric acid with chalcones in glacial acetic acid and phosphorous pentoxide, Part-II

Akhter

Halim

Ahmed

et al. 2017

Bangladesh J. Sci. Ind. Res.

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A number of new 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)-pyrano [2, 3-d] pyrimidin-2, 4-diones (or 2-thioxo-4-ones) (3a-g) have been synthesized in one-step by cyclocondensation of barbituric acid or thiobarbituric acid (1) with arylideneacetophenones (2a-d), in glacial acetic acid in the presence of phosphorous pentoxide. The structures of the compounds 3a-g have been determined by UV, IR, 1H NMR, 13C NMR, mass spectral data and elemental analyses. The compounds 3a-g do not seem to be available in the literature.

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Synthesis of chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones using organic catalysts and their antimicrobial and anticancer activities

Aremu

Singh

et al. 2019

Journal of Heterocyclic Chem

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Chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones were produced by reacting malononitrile, barbituric acid, and aromatic aldehydes together with a DABCO catalyst in an aqueous one‐pot reaction. This is the first report of these compounds being synthesized with DABCO as a catalyst, which produced the compounds in yields in excess of 90%. The 2,4‐difluoro derivative (11) was novel. The structures of the synthesized compounds were elucidated by means of 1H, 13C, and 2D NMR spectroscopy. Compound 2 (2‐Cl derivative) had MBC values of <200μM against both Staphylococcus aureus and MRSA, and the 2‐nitro derivative 5 had an MBC of 191μM against the Gram–ve Escherichia coli. The synthesized compounds were also tested for their anticancer activity against a HeLa cell line, where all the compounds showed better activity (IC50 values between 129μM and 340μM) than 5‐fluorouracil, a commonly known anticancer drug.

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A One Pot Synthesis of 5, 7-diaryl-1,5-dihydro (or 1, 2, 3, 5-tetrahydro)- pyrano[2, 3-D] pyrimidin-2, 4-diones (or 2-thioxo-4-ones)

Cited by 4 publications

References 12 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)

One step cyclocondensation of (thio) barbituric acid with chalcones in glacial acetic acid and phosphorous pentoxide, Part-II

Synthesis of chloro, fluoro, and nitro derivatives of 7‐amino‐5‐aryl‐6‐cyano‐5H‐pyrano pyrimidin‐2,4‐diones using organic catalysts and their antimicrobial and anticancer activities

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