Non-steroidal anti-inflammatory drugs. III. Structure of indoprofen: 2-[4-(1-oxo-2-isoindolinyl)phenyl]propionic acid

Ravikumar, K.

doi:10.1107/s0108270193007450

Cited by 9 publications

(6 citation statements)

References 6 publications

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“…We now report the synthesis of a second drug. This time we used the VNS−alkylation protocol to make Indoprofen ( 21 ), a member of the arylpropionic acid nonsteroidal antiinflammatory drugs …”

Section: Resultsmentioning

confidence: 99%

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNS_AR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

et al. 2002

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The intermediate anion derived from the vicarious nucleophilic substitution (VNS) of hydrogen reacts with a series of alkyl halides to generate the corresponding alpha-alkylated conventional VNS product in a one-pot process. This one-pot VNS-alkylation reaction offers a convenient route to a range alpha-substituted nitrobenzyl phosphine oxides, sulfones, and esters via a three-component coupling reaction. Reactions of alpha-chloroethyl phenyl sulfone (14) and ethyl 2-chloropropionate (16) with nitrobenzene followed by subsequent addition of an alkylating agent give a series of sulfones and esters bearing an alpha-aryl quaternary center. The VNS-alkylation protocol has been applied to the synthesis of derivatives of Indoprofen from nitrobenzene using readily available inexpensive starting materials. Indoprofen itself was prepared using the conventional VNS reaction in four steps and 24% overall yield from nitrobenzene.

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Section: Resultsmentioning

confidence: 99%

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNS_AR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

et al. 2002

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“…For example, indoprofen is used in anti‐inflammatory drugs, falipamil demonstrates anti‐ischemic properties, chlortalidone has a diuretic effect, and pestalachloride A is identified as an antifungal drug. [ 1 ] Therefore, the synthesis of this class of compounds caused a great interest of chemists, and various synthetic methods have been developed. [ 2 ]…”

Section: Background and Originality Contentmentioning

confidence: 99%

Metal‐Free Catalyzed Cyclization of N‐Methoxybenzamides to Construct Quaternary Carbon‐Containing Isoindolinones

et al. 2021

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Quaternary carbe | Density functional theory | Annulation | Alkynes | Synthetic methods Through the intramolecular cyclization of N-methoxybenzamides, a simple and efficient method for constructing valuable isoindolinones under metal-free conditions was developed. The reaction was featured by employing low-cost catalyst, simple operation, 100% atomic economy and excellent regioselectivity. Moreover, a detailed computational study on the reaction system has been performed to clarify the mechanism. This protocol tolerated a variety of functional groups and provided a metal-free protocol for the synthesis of chromane-or tetrahydroquinoline-fused isoindolinones in good yields.

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“…The second isomer's structure is very close to a previously reported X-ray structure. 32 A set of selected distances and angles is reported in Table 1. While the distances and angles of the DFT-calculated structures are very close to the experimental data, the dihedral angles, which characterize the rotation of the acid group, differ somewhat from the experimental values.…”

Section: Ground-state Geometriesmentioning

confidence: 99%

Absorption and solvatochromic properties of 2-methylisoindolin-1-one and related compounds: interplay between theory and experiments

et al. 2005

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Non-steroidal anti-inflammatory drugs. III. Structure of indoprofen: 2-[4-(1-oxo-2-isoindolinyl)phenyl]propionic acid

Cited by 9 publications

References 6 publications

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNS_AR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNS_AR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

Metal‐Free Catalyzed Cyclization of N‐Methoxybenzamides to Construct Quaternary Carbon‐Containing Isoindolinones

Absorption and solvatochromic properties of 2-methylisoindolin-1-one and related compounds: interplay between theory and experiments

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Non-steroidal anti-inflammatory drugs. III. Structure of indoprofen: 2-[4-(1-oxo-2-isoindolinyl)phenyl]propionic acid

Cited by 9 publications

References 6 publications

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNSAR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNSAR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

Metal‐Free Catalyzed Cyclization of N‐Methoxybenzamides to Construct Quaternary Carbon‐Containing Isoindolinones

Absorption and solvatochromic properties of 2-methylisoindolin-1-one and related compounds: interplay between theory and experiments

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Product

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A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNS_AR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives

A Three-Component Coupling Process Based on Vicarious Nucleophilic Substitution (VNS_AR)−Alkylation Reactions: An Approach to Indoprofen and Derivatives