Trending strategies for the synthesis of quinolinones and isoquinolinones

Rao, Latchipatula Bhaskara; Sreenivasulu, Chinnabattigalla; Kishore, Dakoju Ravi; Satyanarayana, Gedu

doi:10.1016/j.tet.2022.133093

Cited by 10 publications

(6 citation statements)

References 123 publications

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“…Traditional organic approaches to access them are based on Friedlander, [41] Knorr [42] or Vilsmeier‐Haack [43] protocols working through the condensation between an amide and a carbonyl function. In addition, modern strategies involving homogeneously metal‐catalyzed processes have been developed for their synthesis [40c,44] . Considering the high interest of these compounds, the development of alternative and more sustainable methodologies for obtaining them is a sought as a relevant goal nowadays in organic chemistry and catalysis.…”

Section: Resultsmentioning

confidence: 99%

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

2023

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An efficient heterogeneous silver‐catalyzed α‐alkylation of nitriles and oxindoles using alcohols via borrowing hydrogen strategy has been developed for the first time. The active nanostructured material, namely [Ag/Mg4Al‐LDH], composed by silver nanoparticles (3‐4 nm average particle size) homogeneously stabilized onto a [Mg4Al‐LDH] support with suitable Brönsted basic properties, constitutes a stable catalyst for the sustainable building of novel C‐C bonds from alcohols and C‐nucleophiles. By applying this catalyst, a broad range of α‐functionalized nitriles and oxindoles has been accessed with good to excellent isolated yields and without the addition of external bases. Moreover, the novel silver nanocatalyst has also demonstrated its successful application to the cyclization of N‐[2‐(hydroxymethyl)phenyl]‐2‐phenylacetamides to afford 3‐arylquinolin‐2(1H)‐ones, through a one‐pot dehydrogenation and intramolecular α‐alkylation. Control experiments, kinetic studies and characterization data of a variety of [Ag/LDH]‐type materials confirmed the silver role in the dehydrogenation and hydrogenation steps, while [Mg4Al‐LDH] matrix is able to catalyze condensation. Interestingly, these studies suggest as key point for the successful activity of [Ag/Mg4Al‐LDH], in comparison with other [Ag/LDH]‐type nanocatalysts, the suitable acid‐base properties of this material.

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Section: Resultsmentioning

confidence: 99%

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

2023

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“…27g Many other methods leading to quinoline derivatives from nitroarenes have been well documented in the literature. 27` j k In such cases, many of the reactions involve costly transition elements such as Ru, Pd, and Mo, and harsh reaction conditions are required in the case of Fe/HCl and SnCl 2 to accomplish reductive cyclization.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Synthesis of Quinoline and Quinolin-2(1H)-one Derivatives via Nickel Boride Promoted Reductive Cyclization

et al. 2023

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A mild and efficient approach for the synthesis of diversely substituted quinoline and quinoline-2-one derivatives has been disclosed. In situ-generated nickel boride was proved to be an effective promoter of the reductive cyclization reaction. Broad substrate scope, mild reaction condition, consistent yield and wide range of functional group tolerance are the other notable features of the newly discovered reaction. A large number of quinoline and quinoline -2-one derivatives may be prepared from milligram to multigram scale employing this intramolecular reductive cyclization protocol.

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“…[25][26][27][28][29][30][31][32][33] In addition, palladium-catalyzed coupling strategies have been featured as the key transformations in successful syntheses of natural products and pharmaceutically active molecules. [34][35][36][37][38] An essential objective of organic chemistry is to develop novel and sustainable synthetic strategies for preparing intermediate products/synthons efficiently. In this regard, synthetic chemists are striving to design and develop novel catalysts, effective methodologies, and more ecologically friendly conditions.…”

Section: Introductionmentioning

confidence: 99%

Palladium-Catalyzed Acylation Strategies and Their Applications Towards Biologically Relevant Products

Sreenivasulu¹,

Kishore²,

Satyanarayana³

et al. 2023

Synlett

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Ketones are fundamental synthons in organic synthesis due to their wide range of applications, which include natural products, pharmaceuticals, dyes, fragrances, agrochemicals, and electronic materials. In recent years, direct acylation strategies based on commercially available benchtop aryl halides and aldehydes (alkyl/aryl) have been the prime focus for the construction of alkyl-aryl/aryl-aryl ketones using palladium catalysis under eco-friendly reaction conditions. In this account, we present conceptually developed palladium-catalyzed direct acylation strategies for achieving various carbo- and heterocycles such as ketones, 2-quinolinones, phthalazines, phthalazinones, benzoxazinones, anthraquinones, indenones, and 1,3-dihydroisobenzofurans. Significantly, these direct acylation strategies have been extended to synthesize the natural product neo-lignan and biologically significant molecules such as an n-butylphthalide antiplatelet drug, pitofenone, fenofibrate, a HBV inhibitor, and a PDE-4 inhibitor. This Account will be of interest to synthetic organic chemists wishing to prepare pharmaceutical molecules and natural products.1 Introduction2 Discussion2.1 Palladium-Catalyzed Environmentally Compassionate Acylation2.2 Palladium-Catalyzed Acylations Followed by Intramolecular Aldol Condensation to Afford Indenones2.3 Acylation of Iodo-acetanilides/Iodo-phenyl Acetates: Sequential One-Pot Syntheses of 2-Quinolinones2.4 A One-Pot Diversified Synthesis of Phthalazines, Phthalazinones, and Benzoxazinones2.5 Palladium-Catalyzed Direct Acylation: A One-Pot Relay Synthesis of Anthraquinones2.6 Palladium-Catalyzed Direct Oxidative Coupling of Primary Alcohols with Iodoarenes Leading to Ketones: Application to the Synthesis of Benzofuranones and Indenones3 Conclusion

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Trending strategies for the synthesis of quinolinones and isoquinolinones

Cited by 10 publications

References 123 publications

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Synthesis of Quinoline and Quinolin-2(1H)-one Derivatives via Nickel Boride Promoted Reductive Cyclization

Palladium-Catalyzed Acylation Strategies and Their Applications Towards Biologically Relevant Products

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Trending strategies for the synthesis of quinolinones and isoquinolinones

Cited by 10 publications

References 123 publications

Silver Supported Nanoparticles on [Mg4Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Silver Supported Nanoparticles on [Mg4Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Synthesis of Quinoline and Quinolin-2(1H)-one Derivatives via Nickel Boride Promoted Reductive Cyclization

Palladium-Catalyzed Acylation Strategies and Their Applications Towards Biologically Relevant Products

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Product

Resources

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Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols

Silver Supported Nanoparticles on [Mg₄Al‐LDH] as an Efficient Catalyst for the α‐Alkylation of Nitriles, Oxindoles and Other Carboxylic Acid Derivatives with Alcohols