Synthesis of Novel Furo[3,2‐c]coumarin Derivatives through Multicomponent [4+1] Cycloaddition Reaction Using ZnO/FAp as a Sustainable Catalyst

Kerru, Nagaraju; Gummidi, Lalitha; Gangu, Kranthi Kumar; Maddila, Suresh; Jonnalagadda, Sreekantha B.

doi:10.1002/slct.202000796

Cited by 29 publications

(13 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Optimization. We initially examined the alkylation of 1-methoxy-4-phenylpyridinium tetrafluoroborate (1a•BF4) with 2cyclohexylbenzo-[d] [1,3,2]dioxaborole (CyBCat) as a model system. [34] Methoxypyridium salt 1a•BF4 was prepared by oxidation of 4-phenylpyridine with m-CPBA followed by methylation with the Meerwein's salt (Me3OBF4).…”

Section: Resultsmentioning

confidence: 99%

“…Aromatic heterocyclic compounds, especially nitrogen containing rings, are core elements of vitamins, amino acids, nucleic acids, and alkaloids and thus attract the attention of the synthetic community and the pharmaceutical industry since many years. [1] A recent study has shown that 59% of U.S. FDA approved smallmolecule drugs contain a nitrogen heterocycles. [2] Their late-stage functionalization is of great interest to modify and tune their pharmaceutical properties.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Radical Chain Monoalkylation of Pyridines

Rieder¹,

Meléndez²,

Mulliri³

et al. 2021

Preprint

View full text Add to dashboard Cite

<p>The monoalkylation of N-methoxypyridinium salts with alkyl radicals generated from alkenes (via hydroboration with catecholborane), alkyl iodides (via iodine atom transfer) and xanthates is reported. The reaction proceeds under neutral conditions since no acid is needed to activate the heterocycle and does not require the use of an external oxidant. A rate constant for the addition of a primary radical to N-methoxylepidinium >107 M–1 s–1 was experimentally determined. This rate constant is more than one order of magnitude larger than the one measured for the addition of primary alkyl radical to protonated lepidine demonstrating the remarkable reactivity of methoxypyridinium salts towards radicals. The reaction could be extended to a three component carbopyridinylation of electron rich alkenes including enol esters, enol ethers and enamides.</p>

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Radical Chain Monoalkylation of Pyridines

Rieder¹,

Meléndez²,

Mulliri³

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

“…21 In addition, tetrabutylammonium bromide (TBAB) can be used to catalyze the reaction of 4-hydroxycoumarin with ethyl benzylidenecyanoacetate to synthesize pyrano [3,2-c]coumarin derivatives (Scheme 1b). 22 There have been many related reports on synthetic methods for these compounds using many catalysts, such as metal catalysts (Fe, Cu, Pd), [23][24][25][26][27][28] NaBr, 29 ZnO, [30][31][32] hexamethylenetetramine, 33 and potassium phthalimide. 34 The major disadvantages of using these catalysts are unsatisfactory yields, long reaction times, complicated operations, and high cost.…”

Section: Examples 40-93% Yieldmentioning

confidence: 99%

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

Xie

Yang

et al. 2021

Synthesis

View full text Add to dashboard Cite

4H-Pyrano[3,2-c]coumarin derivatives are an important class of pharmaceutical compounds that are expensive to prepare by previously reported methods. An efficient and green method was developed to obtain these derivatives using the deep eutectic solvent (DES) zinc chloride/acetamide (n:n = 1:4), which acted as both the catalyst and the solvent for the reaction. An aromatic aldehyde, 4-hydroxycoumarin, and cyanoacetate were used as the substrates. The DES, substrate molar ratio, diluent type, temperature, and reaction time were optimized to obtain the 4H-pyrano[3,2-c]coumarin derivatives from a range of aromatic aldehydes in a single step in moderate to high yields and under mild reaction conditions.

show abstract

“…On the other hand, multicomponent reactions (MCRs) have steadily gained significance in synthetic organic chemistry [ 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. MCRs offer many benefits—e.g., greater yields, high atom efficiency, reduced reaction time, high convergence, minimisation of purification requirements and waste generation—compared to multiple-step syntheses [ 20 , 21 , 22 , 23 , 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review

et al. 2021

Self Cite

View full text Add to dashboard Cite

Heterogeneous catalysis plays a crucial role in many chemical processes, including advanced organic preparations and the design and synthesis of new organic moieties. Efficient and sustainable catalysts are vital to ecological and fiscal viability. This is why green multicomponent reaction (MCR) approaches have gained prominence. Owing to a broad range of pharmacological applications, pyranopyrazole syntheses (through the one-pot strategy, employing sustainable heterogeneous catalysts) have received immense attention. This review aimed to emphasise recent developments in synthesising nitrogen-based fused heterocyclic ring frameworks, exploring diverse recyclable catalysts. The article focused on the synthetic protocols used between 2010 and 2020 using different single, bi- and tri-metallic materials and nanocomposites as reusable catalysts. This review designated the catalysts’ efficacy and activity in product yields, reaction time, and reusability. The MCR green methodologies (in conjunction with recyclable catalyst materials) proved eco-friendly and ideal, with a broad scope that could feasibly lead to advancements in organic synthesis.

show abstract

Synthesis of Novel Furo[3,2‐c]coumarin Derivatives through Multicomponent [4+1] Cycloaddition Reaction Using ZnO/FAp as a Sustainable Catalyst

Cited by 29 publications

References 40 publications

Radical Chain Monoalkylation of Pyridines

Radical Chain Monoalkylation of Pyridines

One-Pot Synthesis of 4H-Pyrano[3,2-c]coumarin Derivatives Catalyzed by Deep Eutectic Solvent

Advances in Pyranopyrazole Scaffolds’ Syntheses Using Sustainable Catalysts—A Review

Contact Info

Product

Resources

About