Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds

Chemical Society Reviews, Год журнала: 2024, Номер 53(9), С. 4607 - 4647

Опубликована: Янв. 1, 2024

This review collectively discussed the utilisation of alcohols in various organic transformations and their application toward intermediates drugs, drug derivatives natural product-like molecules.

Язык: Английский

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Designing Cobalt(II) Complexes for Tandem Dehydrogenative Synthesis of Quinoline and Quinazoline Derivatives

Organic Letters, Год журнала: 2024, Номер 26(2), С. 514 - 518

Опубликована: Янв. 9, 2024

In this work, we have constructed three new Co(II) complexes in which steric features govern their structural geometry. The metal ligand-cooperation behavior of the alkoxy arm is utilized to explore catalytic activities these with respect dehydrogenation. A wide range C-3-substituted quinoline and quinazoline derivatives were synthesized high yields. developed protocol's usefulness enhanced by chemoselective transformation different fatty alcohols synthesize heterocycles having distal unsaturation. Various kinetic, mechanistic, control studies conducted comprehend reaction route.

Язык: Английский

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Microwave-assisted synthesis of bioactive heterocycles: An overview

Tetrahedron, Год журнала: 2022, Номер 126, С. 133085 - 133085

Опубликована: Окт. 12, 2022

Язык: Английский

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A Phosphine-Free Air-Stable Mn(II)-Catalyst for Sustainable Synthesis of Quinazolin-4(3H)-ones, Quinolines, and Quinoxalines in Water

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5250 - 5265

Опубликована: Март 30, 2024

The synthesis, characterization, and catalytic application of a new phosphine-free, well-defined, water-soluble, air-stable Mn(II)-catalyst [Mn(L)(H2O)2Cl](Cl) ([1]Cl) featuring 1,10-phenanthroline based tridentate pincer ligand, 2-(1H-pyrazol-1-yl)-1,10-phenanthroline (L), in dehydrogenative functionalization alcohols to various N-heterocycles such as quinazolin-4(3H)-ones, quinolines, quinoxalines are reported here. A wide array multisubstituted quinazolin-4(3H)-ones were prepared water under air following two pathways via the coupling with 2-aminobenzamides 2-aminobenzonitriles, respectively. 2-Aminobenzyl alcohol ketones bearing active methylene group used partners for synthesizing quinoline derivatives, quinoxaline derivatives by vicinal diols 1,2-diamines. In all cases, reaction proceeded smoothly using our [1]Cl air, affording desired satisfactory yields starting from cheap readily accessible precursors. Gram-scale synthesis compounds indicates industrial relevance synthetic strategy. Control experiments performed understand unveil plausible mechanism.

Язык: Английский

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Biogenic synthesis of δ‐MnO₂ nanoparticles: A sustainable approach for C‐alkylation and quinoline synthesis via acceptorless dehydrogenation and borrowing hydrogen reactions

Applied Organometallic Chemistry, Год журнала: 2023, Номер 37(7)

Опубликована: Апрель 26, 2023

The sustainable and environmentally benign biogenic synthesis of manganese‐oxide nanoparticles (MnO 2 NPs) in a single crystalline δ ‐phase its subsequent synthetic utility have been described. synthesized ‐MnO NPs were characterized using scanning electron microscopy (SEM), energy dispersive X‐ray (EDX), diffraction (XRD) analysis techniques. detailed envisages the reduction Mn(VII) to Mn(IV) was facilitated by various phytochemicals present aq. mango leaves extract, avoiding use external ligand source. perceived delta ( ) monoclinic phase, wherein spherical agglomerated morphology displayed with particle size <5 nm. Further, newly developed showcased for alpha‐keto‐alkylation quinoline via hydrogen autotransfer acceptorless dehydrogenative coupling strategy. Moreover, series control experiments, mechanistic elucidation, catalyst recyclability, dye removal study demonstrated.

Язык: Английский

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Greener Approach for Synthesis of δ-MnO₂ Nanoparticles: Access to Pharmaceutically Important Pyrimidines and their Antimicrobial Activity Studies

ACS Applied Bio Materials, Год журнала: 2024, Номер 7(3), С. 1790 - 1800

Опубликована: Фев. 29, 2024

A sustainable approach for pharmaceutically important pyrimidine derivatives is achieved by using biogenically produced single-phase δ-MnO2 NPs under external ligand-free conditions. The phytochemicals that comprise the extract of Areca Nut Husk (ANH) have been discovered to serve as reducing agents. role not only aid in reduction Mn(VII) into Mn(IV), but they also an stabilizing catalyst. establishment was confirmed inveterate FE-SEM, p-XRD, ICP-OES (Mn content = 43.17% w/w), EDX, and with active Mn w/w. series were prepared good yields a one-pot multicomponent synthesis atmospheric In addition, hot filtration tests, control experiments, gram-scale synthesis, mechanistic investigations demonstrated. Additionally, antimicrobial activity studies against Gram-negative bacteria E. coli, growth curve minimum inhibitory concentration studied.

Язык: Английский

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Room-Temperature Synthesis of Biogenic δ-MnO₂ NPs for the Dehydrogenative Coupling of Diamines with Alcohols for Benzimidazole and Quinoxaline Synthesis: An Efficient Catalyst for Electrochemical Applications

Langmuir, Год журнала: 2023, Номер 39(44), С. 15474 - 15486

Опубликована: Окт. 24, 2023

An efficient, unique, and eco-friendly biogenic synthesis of single-crystalline δ-phase manganese oxide nanoparticles (MnO2 NPs) using Gliricidia sepium leaves (GSL) extract at room temperature has been revealed for the first time. The active chemicals present in GSL were found to serve as both reducing stabilizing agents. catalyst shows an excellent surface area 301.13 m2 g-1, a mean pore diameter 4.01 nm, 39.97% w/w metal content. reactivity synthesized was demonstrated by achieving one-pot benzimidazoles quinoxalines via acceptorless dehydrogenative coupling strategy utilizing biorenewable alcohols. release hydrogen gas observed only side product proven its successful utilization alkene reduction which supports mechanistic elucidation. useful byproduct highlights scientific importance methodology. Additionally, gram-scale recyclability studies are deliberated. Importantly, δ-MnO2 NP exhibited superior catalytic activity high durability toward evolution reaction alkaline media, highlighting dual use catalyst. NPs attain current density 10 mA/cm2 overpotential 154 mV with Tafel slope 119 mV/dec.

Язык: Английский

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Skeletal Editing Through Single Atom Insertion and Transmutation: An Insight into A New Era of Synthetic Organic Chemistry

Synthesis, Год журнала: 2024, Номер 56(24), С. 3793 - 3814

Опубликована: Авг. 20, 2024

Abstract Considering the importance of heterocycles, significantly represented in medicinal chemistry and drug development, single-atom insertion technique transmutation strategy provide productive approaches towards complicated molecular structures through heterocycle diversification. It shows a potentially powerful approach for modifying complex substrates concisely chemospecifically. Although skeletal editing applies to cyclic acyclic compounds, this review focuses on diversification carbo- heterocyclic compounds synthesizing various medicinally important molecules via technique. The classification system is based recent critical historical methods as applied aromatic rings. 1 Introduction 2 Skeletal Editing Carbon-Atom Insertion 2.1 Indoles Pyrroles Derivatives: into C=C Bond 2.2 Pyrazole Indazole an N–N 2.3 CF3 Group Heteroarenes 2.4 Imidazole C–N 2.5 Atom-to-Atom Transmutation 3 N-Atom 3.1 Nitrogen-Atom Carbocycles 3.2 Heterocycles 3.3 Carbon Nitrogen Molecular Isotopic 4 Conclusion

Язык: Английский

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Hydrogenation of N-Heterocycles by a Well-Defined Phosphine-Free Manganese Catalyst Using Ammonia Borane

Organometallics, Год журнала: 2023, Номер 42(23), С. 3385 - 3396

Опубликована: Ноя. 27, 2023

Efficient hydrogenation of N-heterocycles employing low-cost and easy-to-access catalysts is highly desirable as the corresponding hydrogenated have significant importance. Herein, we disclosed well-defined phosphine-free Mn-catalyzed effective transfer (TH) various using ammonia borane hydrogen source. In this work, a series Mn(I) complexes were synthesized to investigate importance ligand backbone containing benzimidazole N–H, amine soft sulfur atom. Reactivity studies these Mn revealed that proton-responsive Mn1 complex bearing N–H proton benzimidazole, amine, hemilabile arm was found be most effective. The capability procedure verified by synthesis several biologically active compounds. Mechanistic pathways established performing control reactions kinetic experiments.

Язык: Английский

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Orthometallated Pd(ii) C^N^S pincer complex catalyzed sustainable synthesis of bis(indolyl)methanesviaacceptorless dehydrogenative coupling of alcohols

Catalysis Science & Technology, Год журнала: 2023, Номер 13(11), С. 3358 - 3365

Опубликована: Янв. 1, 2023

New orthometallated Pd( ii ) C^N^S pincer catalyst-mediated sustainable and cost-effective synthesis of pharmacologically important bis(indolyl)methanes (23 examples up to 95% yield) via ADC is reported.

Язык: Английский

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