One-pot multicomponent synthesis of benzophenazine tethered tetrahydropyridopyrimidine derivatives

Darakshan,; Parvin, Tasneem

doi:10.1007/s11030-022-10426-4

Cited by 8 publications

(2 citation statements)

References 44 publications

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“…Tetrahydropyridopyrimidines are employed as irreversible covalent inhibitors of KRAS-G12C as well as PDE10A inhibitors. 97 Parvin achieved 98 a straightforward, easy-to-use, and environmentally friendly green methodology for the one-pot, four-component reaction of cinnamaldehyde/crotonaldehyde, 2-hydroxy-1,4-naphthoquinone, o -phenylenediamine, and 1,3-dimethyl-6-amino uracil in ethanol as a solvent under reflux conditions by utilizing p -TSA as a catalyst (Scheme 60). Three bioactive moieties, including tetrahydropyridine, pyrimidine, and benzophenazine, are present in the hybrid products.…”

Section: Synthesis Of Fused-heterocyclic Compoundsmentioning

confidence: 99%

p-Toluenesulfonic acid-promoted organic transformations for the generation of molecular complexity

Pal,

Das,

Bhunia

2024

Org. Biomol. Chem.

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Section: Synthesis Of Fused-heterocyclic Compoundsmentioning

confidence: 99%

p-Toluenesulfonic acid-promoted organic transformations for the generation of molecular complexity

Pal,

Das,

Bhunia

2024

Org. Biomol. Chem.

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“…Further reaction with NH 4 OH in ethanol under reflux conditions led to the synthesis of 2,4,6-triaryl pyridine derivatives. [34] As part of our ongoing research work [35] herein, we developed a simple and efficient synthetic method to synthesize polycyclic pyrrolopyridine derivatives by a two-step reaction through the synthesis of 1,5diketones (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Polycyclic Pyrrolopyridine Derivatives via Multicomponent Synthesis of 1,5‐Diketones

Chaurasia,

Parvin

2024

ChemistrySelect

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A simple, two‐step process was developed for the easy access of polycyclic pyrrolopyridine derivatives. The first step involves a multicomponent reaction of aryl glyoxal, cyclohexane‐1,3‐dione derivatives and 2‐amino‐1,4‐napthoquinone in AcOH: H2O (1 : 1 v/v) under reflux conditions which led to the formation of 1,5‐diketones in 15 min of reaction time. In the second step, the reaction of ammonium acetate with 1,5‐diketones in AcOH under reflux conditions resulted the formation of polycyclic pyrrolopyridine derivatives. All the products were characterized by FTIR, 1H NMR, 13C NMR and HRMS. The single crystal XRD of one compound was recorded to further confirm the structure of the product. The presence of several bioactive moieties in our product, simple reaction process, metal‐free reaction conditions, easy purification method, and good yields of the products are the notable features of this methodology.

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A comparative study for the efficiency of Pd (II) and Fe (III) complexes as efficient catalysts for synthesis of dihydro‐7H‐5‐thia‐hexaaza‐s‐indacen‐6‐one derivatives supported with DFT approach

El‐Remaily,

Eskander,

Elhady

et al. 2024

Applied Organom Chemis

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Two novel complexes were synthesized by the reaction of benzothiazol‐pyrimidin‐2‐ylidene ligand (BTP) with Pd (II) and Fe (III) ions. A variety of various spectral and analytical methods (infrared, 1H/NMR, 13C/NMR, electronic spectra, CHN analyses, mass spectra, thermogravimetric analysis, and magnetic susceptibility) were used to characterize the investigated BTP ligand and its complexes. Correlation of experimental results with density functional theory calculation proves that the geometry of BTP‐Fe complex is octahedral, whereas BTP‐Pd complex is square planner. The catalytic effectiveness of BTP complexes were tested for three‐component condensation process under moderate and environmentally friendly reaction conditions. Moreover, the effects of different Lewis acid, basic, and ionic liquid catalysts, as well as solvent and catalyst dose on the catalytic reaction were investigated. Both catalysts demonstrated strong catalytic capability in the carefully regulated ideal reaction circumstances. Heterogeneous catalyst BTP‐Pd exhibited superior catalytic performance compared to homogeneous catalyst BTP‐Fe. All products were obtained in high TOF (turnover frequency) numbers in the presence of these catalysts, which indicate the high efficiency of these catalysts in the synthesis of dihydro‐7H‐5‐thia‐hexaaza‐s‐indacen‐6‐one derivatives. Moreover, the two catalysts' recycling and reusability in reactions were also investigated. Heterogeneous BTP‐Pd catalyst could be reused up to seven times with high efficiency, but the homogeneous catalyst (BTP‐Fe) could only be recycled up to four times. Furthermore, the mechanism of catalytic reaction was suggested and supported by DFT calculation. The simplicity, safety, stability, use of commercially available catalysts, quick reaction times, and excellent yields make it promising for future industrial use.

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One-pot multicomponent synthesis of benzophenazine tethered tetrahydropyridopyrimidine derivatives

Cited by 8 publications

References 44 publications

p-Toluenesulfonic acid-promoted organic transformations for the generation of molecular complexity

p-Toluenesulfonic acid-promoted organic transformations for the generation of molecular complexity

Synthesis of Polycyclic Pyrrolopyridine Derivatives via Multicomponent Synthesis of 1,5‐Diketones

A comparative study for the efficiency of Pd (II) and Fe (III) complexes as efficient catalysts for synthesis of dihydro‐7H‐5‐thia‐hexaaza‐s‐indacen‐6‐one derivatives supported with DFT approach

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