Synthesis of Functionalized Dihydropyrido[2,3-d]pyrimidines in Aqueous Medium

Balalaie, Saeed; Esmaeilabadi, Hamed; Mehrparvar, Saber; Röminger, Frank; Hamdan, Fatima; Bijanzadeh, Hamid Reza

doi:10.1055/s-0036-1591869

Cited by 5 publications

(3 citation statements)

References 4 publications

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“…The activity was first checked among the simplest of N‐heterocycles (Figure 6) such as pyridine. 2‐aminopyridine (entry 1), which is considered as an important skeleton in medicinal chemistry [59,60] . The product was obtained within 10 min with 100 % selectivity to amines.…”

Section: Resultsmentioning

confidence: 99%

“…2-amino-pyridine (entry 1), which is considered as an important skeleton in medicinal chemistry. [59,60] The product was obtained within 10 min with 100 % selectivity to amines. Amino group, being an electron donating group makes the aromatic pyridine system more stable as compared to the electron withdrawing nitro group thereby favouring the reduction.…”

Section: Substrates Scopementioning

confidence: 99%

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Oxygen Vacancy Mediated Reactivity of CaO/CuO Composite for the Synthesis of Amino‐N‐heterocycles

Rajendran,

Madampadi,

Shee

et al. 2023

ChemCatChem

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Utilising the oxygen‐vacancy‐mediated reactivity of CaO/CuO and hydrazine monohydrate in isopropyl alcohol at 353 K, a variety of amino‐derivatives of N‐heterocycles, including pyridine, indole, quinoline, isoquinoline, and benzothiazole, have been selectively synthesised by reducing their nitro analogues. It is demonstrated that CaO/CuO composite is a reusable, solvent‐resilient solid reducing agent that can reduce a variety of nitro‐N‐heterocyclic substrates. The critical role of the structure of CaO/CuO on the nitro‐reduction activity has been studied using spectroscopy and microscopy. DFT simulations indicate the facile formation of oxygen vacancies (EO,vac =‐ 43.4 kJ/mol) on the interface of CaO/CuO surface under reducing environment. The presence of CaO facilitated a stronger interaction of the nitro‐substrate on the oxygen vacant CuO (111) surface, resulting into a significantly lower activation energy (Ea = 21.9 kJ/mol) for N‐O dissociation. The reaction could be scaled up from 1 to 12 mmol of substrate. CaO/CuO is a reusable and a cost‐effective alternative to the conventional catalyst (Pd/C, Pt/C).

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Section: Resultsmentioning

confidence: 99%

Section: Substrates Scopementioning

confidence: 99%

Oxygen Vacancy Mediated Reactivity of CaO/CuO Composite for the Synthesis of Amino‐N‐heterocycles

Rajendran,

Madampadi,

Shee

et al. 2023

ChemCatChem

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“…Recently Balalaie et al 47,48 synthesized similar compounds using water as a solvent to develop an environmentally friendly process and to minimize the use of organic solvents with the help of heating. This process contains heating at 50 1C and a phosphate-containing nitrogen source.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted catalyst-free multicomponent one-pot green synthesis of highly functionalized aminocyanopyridines and (4-hydroxy)quinolines in aqueous medium and its in silico studies

et al. 2022

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Regiocontrolled Synthesis of Fused Heterocyclic Skeletons Containing Pyranocoumarin Backbones

et al. 2019

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A convenient, highly efficient regioselective strategy for the synthesis of chromeno [3',4'-5,6]pyrano[2,3-b]quinoline is described. The reaction proceed through three-component reaction of 2-chloro-3-formylquinoline, malononitrile and 4-hydrox-ycoumarin in the presence of 10 mole% diammonium hydrogen phosphate (DAHP) in aqueous media at room temperature. It is a domino Knoevenagel condensation/ Michael addition and regiocontrolled cyclization reaction.

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Synthesis of Functionalized Dihydropyrido[2,3-d]pyrimidines in Aqueous Medium

Abstract: Synthesis of functionalized 2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one from a cascade reaction between 3-formylchromone, malononitrile, diammonium hydrogen phosphate, and aromatic aldehydes in aqueous media is described.

Cited by 5 publications

References 4 publications

Oxygen Vacancy Mediated Reactivity of CaO/CuO Composite for the Synthesis of Amino‐N‐heterocycles

Oxygen Vacancy Mediated Reactivity of CaO/CuO Composite for the Synthesis of Amino‐N‐heterocycles

Microwave-assisted catalyst-free multicomponent one-pot green synthesis of highly functionalized aminocyanopyridines and (4-hydroxy)quinolines in aqueous medium and its in silico studies

Regiocontrolled Synthesis of Fused Heterocyclic Skeletons Containing Pyranocoumarin Backbones

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