Application of nitriles on the synthesis of 1,3-oxazoles, 2-oxazolines, and oxadiazoles: An update from 2014 to 2021

Facchinetti, Victor; Gomes, Cláudia R. B.; Souza, Marcus V. N. de

doi:10.1016/j.tet.2021.132544

Cited by 14 publications

(5 citation statements)

References 65 publications

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“…SAR analysis demonstrated that the addition of the 3,4-dichlorophenethyl moiety not only inhibits oxidative processes but also improves the pharmacokinetic properties of this class of organic compounds. [87] Finally, several studies [88][89][90][91] are urgently needed to gain a better understanding of the many biological effects of 1,2,4-oxadiazoles.…”

Section: Antidiabetic Agentsmentioning

confidence: 99%

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A comprehensive review of recent advances in the biological activities of 1,2,4‐oxadiazoles

Hendawy

2022

Archiv der Pharmazie

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Nitrogen heterocycles play an essential role in medication development. The 1,2,4‐oxadiazole heterocycle has been extensively studied, yielding a large variety of molecules with varied biological functions. The 1,2,4‐oxadiazole shows bioisosteric equivalency with ester and amide moieties. In recent years, the 1,2,4‐oxadiazole nucleus has received a lot of attention in medicinal chemistry. It was thought to be a pharmacophore component in the production of biologically intriguing drugs. This review presents a comprehensive overview of the recent achievements in the biological activities of 1,2,4‐oxadiazoles as potential antimicrobial, anticancer, anti‐inflammatory, neuroprotective, and antidiabetic agents. The structure–activity relationship and mechanisms of action are also reviewed.

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Section: Antidiabetic Agentsmentioning

confidence: 99%

“…Finally, several studies [ 88–91 ] are urgently needed to gain a better understanding of the many biological effects of 1,2,4‐oxadiazoles.…”

Section: Biological Characteristics Of 124‐oxadiazolesmentioning

confidence: 99%

A comprehensive review of recent advances in the biological activities of 1,2,4‐oxadiazoles

Hendawy

2022

Archiv der Pharmazie

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“…Acetonitrile can also be utilized in the construction of a variety of heterocyclic compounds. Examples include the synthesis of pyridine, oxazole, and tetrazole [17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Advances in the Application of Acetonitrile in Organic Synthesis since 2018

Zhong

Zhang²,

Luo

et al. 2023

Catalysts

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Acetonitrile is commonly used as an organic solvent and can also be used as an important intermediate in organic synthesis. Its widespread use has led to the development of new methods for the synthesis of a variety of important compounds. In the past decades, the conversion reactions of acetonitrile as a building block have become one of the most-attractive fields in organic synthesis. Especially in the field of electrochemical conversions involving acetonitrile, due to its good conductivity and environmentally friendly features, it has become a powerful and compelling tool to afford nitrogen-containing compounds or nitrile-containing compounds. In this review, we mainly discuss the research progress involving acetonitrile in the past five years, covering both conventional synthesis methods and electrochemical synthesis. Besides, a detailed discussion of the substrate scope and mechanistic pathways is provided.

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“…Cyano‐groups are present in various bioactive compounds, pharmaceuticals, agrochemicals, dyes, electronic materials and, in addition, they serve as a chemical multi‐tool for a whole range of different reactions. [1] Cyano‐groups are precursors for primary and secondary amides, amidines, imidines, aldehydes, ketones, carboxylic acids, amines, [2] nitrile‐oxides, nitrile imines and N ‐heterocyclic compounds, [3] cyanamides, thiocyanates and cyanate esters. [4] As a general trend, nitriles evoke similar odour perceptions as their corresponding aldehydes.…”

Section: Introductionmentioning

confidence: 99%

Organic Acid to Nitrile: A Chemoenzymatic Three‐Step Route

et al. 2022

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Various widely applied compounds contain cyano-groups, and this functional group serves as a chemical handle for a whole range of different reactions. We report a cyanide free chemoenzymatic cascade for nitrile synthesis. The reaction pathway starts with a reduction of carboxylic acid to aldehyde by carboxylate reductase enzymes (CARs) applied as living cell biocatalysts. The second -chemical -step includes in situ oxime formation with hydroxylamine. The final direct step from oxime to nitrile is catalyzed by aldoxime dehydratases (Oxds). With compatible combinations of a CAR and an Oxd, applied in one-pot two-step reactions, several aliphatic and aryl-aliphatic target nitriles were obtained in more than 80% conversion. Phenylacetonitrile, for example, was prepared in 78% isolated yield. This chemoenzymatic route does not require cyanide salts, toxic metals, or undesired oxidants in contrast to entirely chemical procedures.

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Application of nitriles on the synthesis of 1,3-oxazoles, 2-oxazolines, and oxadiazoles: An update from 2014 to 2021

Cited by 14 publications

References 65 publications

A comprehensive review of recent advances in the biological activities of 1,2,4‐oxadiazoles

A comprehensive review of recent advances in the biological activities of 1,2,4‐oxadiazoles

Advances in the Application of Acetonitrile in Organic Synthesis since 2018

Organic Acid to Nitrile: A Chemoenzymatic Three‐Step Route

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