Selenium‐Catalyzed Reductive Carbonylation of 2‐Nitrophenols to2‐Benzoxazolones

Wang, Xiaofang; Lü, Gang; Xue, Yan; Lü, Shiwei

doi:10.1002/ejoc.200400561

Cited by 41 publications

(17 citation statements)

References 31 publications

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“…Since selenium is not a transition metal, these reactions have not been included in this review, but the older examples are cited in our previous reviews, that were focused on the use of CO. [1][2] A few papers have been published in more recent years, which had not been included in those reviews. [221][222][223][224]…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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Nitroarenes are the entry point for the production of most nitrogen‐containing aromatic compounds. Thus, any transformation that leads directly from them to the final product allows saving one or more synthetic steps. This review deals with homogeneously catalyzed reactions leading to the formation of N‐heterocyclic compounds from nitroarenes or nitroalkenes in one pot. Reactions that lead to the intermediate formation of amines are not considered. Carbon monoxide is the most often employed reductant because it allows selective reactions, is cheap, and only produces CO2 as stoichiometric byproduct. However, the difficulty in handling pressurized CO has stimulated in recent years the development of CO‐surrogates, that is molecules able to liberate CO during the reaction. The use of phosphines and diols has also been developed in conjunction with molybdenum catalysts. The review focusses in more detail on the literature in the period 2006–2018, but reference to earlier work is made when necessary to put recent results in a more general context.

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Section: Miscellaneous Reactionsmentioning

confidence: 99%

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

2019

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“…1,2,3-Triazole compounds have attracted attention because they exhibit a broad variety of biological activities. For example, compounds such as 1 are active against Mycobacterium tuberculosis [7]; other compounds act as anticancer 2 [8], antifungal 3 [9], or antitumor agents 4 [10], Scheme 1. Some biomedical applications have been described, for example, the labelling of biomolecules [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

Sarmiento-Sánchez

Ochoa-Terán

Rivero

2014

The Scientific World Journal

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The efforts for synthesis of enantiomerically pure bis-(1,2,3-triazolylmethyl)amino esters 6 are reported in good yields from an in situ generated α-azidomethyl ketone. Optimum experimental conditions were established for preparation of α-halomethyl ketones 10 and α-N,N-dipropargylamino esters 11, all derived from α-amino acids. The starting materials reacted under conventional click chemistry conditions, revealing a specific reactivity of bromomethyl ketones over chloromethyl ketones. The antioxidant activity of compounds 6 was assayed by DPPH method. The compound 6c with an IC50 of 75.57 ± 1.74 μg mL−1 was the most active. Technically, this methodology allows the preparation of a combinatorial library of analogues with different structural characteristics depending on the nature of the modified α-amino acids employed in the synthesis.

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“…[21][22][23] Conventionally,2 -imidazolidinones and other cyclic ureas are synthesized by the reaction of diamines with several reagents such as carbonyldiimidazole, [24] trichloromethyl chloroformate, [25] organic carbonates, [26,27] dithiocarbonate, [28] carbonyl selenide, [29,30] and carbon monoxide (Scheme 1). [31,32] The reported methods for the synthesis of 4-imidazolidinones are reactiono fg lycinamide derivatives with carbonyl compounds under acidic [33,34] and basic [35,36] conditions (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Imidazolidinones and Imidazolidine‐2,4‐diones as Antiviral Agents

Swain

Mohanty

2019

ChemMedChem

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Imidazolidinones and imidazolidine‐2,4‐diones are important classes of heterocyclic compounds that possess potent activities against several viruses such as dengue virus, enterovirus, hepatitis C virus (HCV), and human immunodeficiency virus (HIV). The first imidazolidinone derivative as an anti‐HIV agent was reported in 1996. Imidazolidinones inhibit HIV aspartic protease activity, and also act as CCR5 co‐receptor antagonists. Significant effort has been devoted to the design of various imidazolidinone analogues that are active against drug‐resistant HIV strains, with fewer side effects. Different scaffolds have been designed through both rational drug design strategies and computer‐aided drug design. Imidazolidinones have been found to be potent against HIV, and preclinical studies are currently in progress. There are some reports of imidazolidinones as having both anti‐HCV and anti‐dengue virus activity, and more research has yet to be done along these lines. These compounds inhibit NS3 serine protease of HCV, and NS2B‐NS3 protease of dengue virus. Pyridyl‐imidazolidinones possess very specific and potent activity against human enterovirus 71 (EV71) by targeting the EV71 capsid protein VP1, and inhibiting viral adsorption and/or viral RNA uncoating.

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Selenium‐Catalyzed Reductive Carbonylation of 2‐Nitrophenols to2‐Benzoxazolones

Cited by 41 publications

References 31 publications

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes

Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

Imidazolidinones and Imidazolidine‐2,4‐diones as Antiviral Agents

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