Phosphorylation of organic compounds by phosphoric anhydride. Part 1. Phosphorylated benzanilides

Efremov, D.A.; Oberlander, Eva A.; Tebby, John C.; Zavlin, P. M.; Грибанов, А. В.

doi:10.1039/p19940002443

Cited by 7 publications

(2 citation statements)

References 10 publications

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“…Using general method A (100 mg of benzoic acid, 322 mg of triphenylphosphine, 223 mg of N -chlorophthalimide, 332 mg of 2,4,6-trimethylaniline, and 3 mL of toluene), the product was purified by column chromatography ( R f = 0.28, 100% DCM) and isolated in 56% yield, 110 mg. Spectra data matched reported data …”

Section: Methodssupporting

confidence: 58%

Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

2020

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We describe a methodology for the amidation of carboxylic acids by generating phosphonium salts in situ from N-chlorophthalimide and triphenylphosphine. Aliphatic, benzylic, and aromatic carboxylic acids can be transformed into their amide counter parts using primary and secondary amines. This functional group interconversion is achieved at room temperature in good to excellent yields. Mechanistic work shows the in situ formation of chloro- and imido-phosphonium salts that react as activating agents for carboxylic acids and generate an acyloxy-phosphonium species.

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Section: Methodssupporting

confidence: 58%

Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

2020

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“…In the case of barbituric acids, the products were N-phosphorylated [3]. The reaction of phosphoric anhydride with benzanilides was recently reported, and evidence for the for- Dedicated mation of both N and O phosphorylated amides was presented [4].…”

Section: Introductionmentioning

confidence: 97%

Reactions of phosphoric anhydride with acyclic amides. Synthesis of amidines and imides

Oberlander

Tebby

1998

Heteroatom Chem.

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ChemInform Abstract: Phosphorylation of Organic Compounds by Phosphoric Anhydride. Part 1. Phosphorylated Benzanilides.

et al. 1995

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Phosphorylation of organic compounds by phosphoric anhydride. Part 1. Phosphorylated benzanilides

Cited by 7 publications

References 10 publications

Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

Amide Synthesis through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

Reactions of phosphoric anhydride with acyclic amides. Synthesis of amidines and imides

ChemInform Abstract: Phosphorylation of Organic Compounds by Phosphoric Anhydride. Part 1. Phosphorylated Benzanilides.

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