A short synthesis of troglitazone: An antidiabetic drug for treating insulin resistance

Cossy, Janine; Menciu, Cecilia; Rakotoarisoa, Haja; Kahn, Philippe; Desmurs, Jean‐Roger

doi:10.1016/s0960-894x(99)00630-7

Cited by 16 publications

(9 citation statements)

References 3 publications

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“…For example, vitamin E is a radical scavenger having antioxidant properties and it is also potent against lipid peroxidation . Troglitazone belongs to a class of thiazolidinediones and used as anti‐inflammatory and antidiabetic drug . Catechin is a metabolite with antioxidant properties .…”

Section: Methodsmentioning

confidence: 99%

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Pd^II‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Shukla

Pal

Volla

2018

Chemistry An Asian Journal

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A highly regio‐ and stereoselective PdII‐catalyzed cascade synthesis of biologically relevant chromane derivatives from easily available enynes was developed under operationally simple conditions. The cascade reaction consists of nucleopalladation of alkynes, insertion of the alkene and protonation. When CuCl2 was employed as nucleophile, a cis‐chloropalladation initiates the cascade. Whereas in the case of AcOH, a trans‐acetoxypalladation takes place.

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Section: Methodsmentioning

confidence: 99%

“…[14] Troglitazoneb elongst oa class of thiazolidinediones and used as anti-inflammatory and antidiabetic drug. [15] Catechin is am etabolite with antioxidant properties. [16] As ar esult, variouss ynthetic approaches were demonstrated for the synthesis of chromanes.…”

mentioning

confidence: 99%

Pd^II‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Shukla

Pal

Volla

2018

Chemistry An Asian Journal

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“…This approach was later applied in the synthesis of troglitazone. 121 In formed in 60% yield. Together with this study, the authors have also studied Mukaiyama aldol reaction using triflimide as catalyst.…”

Section: Friedel−crafts and Related Reactionsmentioning

confidence: 98%

“…Therefore, this protocol could be highly attractive for large-scale synthesis. This approach was later applied in the synthesis of troglitazone …”

Section: Reactions Catalyzed or Mediated By Triflimidementioning

confidence: 99%

Triflimide (HNTf₂) in Organic Synthesis

2018

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Triflimide (HNTf2) is a commercially available and highly versatile super Brønsted acid. Owing to its strong acidity as well as good compatibility with organic solvents, it has been widely employed as an exceptional catalyst, promoter, or additive in a wide range of organic reactions. On many occasions, triflimide has been demonstrated to outperform triflic acid (TfOH). The uniquely outstanding performance of triflimide also benefits from the low nucleophilicity and noncoordinating property of its conjugate base (Tf2N–). Therefore, it has been employed as a precursor toward a variety of cationic metal complexes or organic intermediates with enhanced reactivity or catalytic activity. In this Review, we describe these features and applications of triflimide in organic synthesis, including its synthesis, physical properties, and role as catalyst or promoter in organic reactions. At the end of this Review, another closely related reagent, triflidic acid (HCTf3), is also briefly introduced.

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“…9 Troglitazone is used as an anti-inflammatory and antidiabetic drug. 10 Catechin has antioxidant properties. 11 Therefore, the synthesis of oxygencontaining heterocyclic compounds plays an important role in organic synthesis.…”

Section: ■ Introductionmentioning

confidence: 99%

Propargyl Chalcones’ Radical Annulation/Sulfonation Reaction: Efficient Synthesis of Benzo[b]oxepin-5(2H)-one and Chromane Derivatives

Zhang

et al. 2022

J. Org. Chem.

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A novel and facile methodology for the synthesis of sulfonated benzo[b]oxepinone and chromane derivatives was reported by the reaction of propargyl chalcones with arylsulfonyl chloride via radical cascade annulation/sulfonation under laboratory conditions. Readily available propargyl chalcones, commercialized arylsulfonyl chloride, and simple reaction conditions make this six(seven)-membered oxygen-containing heterocycles’ synthetic strategy more attractive and with significant application values.

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A short synthesis of troglitazone: An antidiabetic drug for treating insulin resistance

Cited by 16 publications

References 3 publications

Pd^II‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Pd^II‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Triflimide (HNTf₂) in Organic Synthesis

Propargyl Chalcones’ Radical Annulation/Sulfonation Reaction: Efficient Synthesis of Benzo[b]oxepin-5(2H)-one and Chromane Derivatives

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A short synthesis of troglitazone: An antidiabetic drug for treating insulin resistance

Cited by 16 publications

References 3 publications

PdII‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

PdII‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Triflimide (HNTf2) in Organic Synthesis

Propargyl Chalcones’ Radical Annulation/Sulfonation Reaction: Efficient Synthesis of Benzo[b]oxepin-5(2H)-one and Chromane Derivatives

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Product

Resources

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Pd^II‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Pd^II‐Catalyzed Cascade Synthesis of Chromane Derivatives Initiated by cis‐Chloropalladation or trans‐Acetoxypalladation

Triflimide (HNTf₂) in Organic Synthesis