N-Acylation of amides with acid anhydrides by way of dual activation using MgBr2·OEt2

Yamada, Shinji; Yaguchi, Setsuko; Matsuda, Kaori

doi:10.1016/s0040-4039(01)02208-0

Cited by 28 publications

(9 citation statements)

References 21 publications

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“…The formation of arylamides through reaction of aryl amines with acid chlorides is a classic reaction . Acylation of amides with acyl halides to give acyclic imides is also well known, but usually activation of either the amide or the acyl halide, or vigorous reaction conditions are required …”

Section: Resultsmentioning

confidence: 99%

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Frogley

Perera

Wright

2017

Chemistry A European J

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The first examples of amino-substituted fused-ring metallabenzenes, the cationic iridabenzofuran [Ir(C H O{NH -2}{OMe-7})(CO)(PPh ) ][O SCF ] (5) and neutral analogue Ir(C H {NH -2}{OMe-7})Cl(PPh ) (6), can be prepared by reduction of the corresponding nitro-substituted iridabenzofurans with zinc and concentrated hydrochloric acid. N-functionalised derivatives of 5 and 6 are formed through alkylation, sulfonylation or acylation. Thus, consecutive treatments with methyl triflate and base gives the corresponding trimethylammonium-substituted iridabenzofurans while sulfonamide derivatives are formed with p-toluenesulfonyl chloride. N-Acylation of 5 or 6 with acid chlorides, however, selectively form either amide or imide products depending on the charge on the metal and the steric size of the acid chloride. Cationic 5 gives amide substituted products regardless of the conditions whereas neutral 6 rapidly undergoes di-N-acylation with excess benzoyl chloride under mild conditions to give the imide-substituted product Ir(C H O{N[C(O)Ph] -2}{OMe-7})Cl(PPh ) (13). Selective mono-acylation of 6 can be achieved with one equivalent of benzoyl chloride or with excess of the sterically congested pivaloyl chloride.

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Section: Resultsmentioning

confidence: 99%

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Frogley

Perera

Wright

2017

Chemistry A European J

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“…H,13 C,19 F and 31 P NMR spectra were recorded at 300, 75, 282 and 121 MHz, respectively, on a Bruker AC-300 with TMS as internal reference (for 1 H and 13 C), CHF3 (forDownloaded by [University of Nebraska, Lincoln] at 04:53 06 October 2015…”

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confidence: 99%

Reactivity of Phosphonothioamidates with Acid Chlorides and Primary Amines: Synthesis and Conformational Study of N-Acylated Phosphonothioamidates and Phosphonoamidines

Omrani

Akacha

2015

Phosphorus, Sulfur, and Silicon and the Related Elements

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Various N-acyl phosphonothioamidate derivatives, 2, were obtained from N-acylation of phosphonothioamidates, 1, with different acid chlorides. Phosphonoamidines, 3, were prepared in high yields by reacting phosphonothioamidates, 1, with primary amines at room temperature, ro short reaction periods. All compounds were characterized on the basis of IR and NMR spectroscopy ( 1 H, 13 C, 19 F and 31 P) and in some cases by elemental analysis and calculations using Density Functional Theory (DFT)-B3LYP// 3-21G+** and evolution study by 31 P-NMR and 19 F-NMR spectroscopy using an external lock with D 2 O.

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“…Recently, N-acylation of amides/oxazolidinones with acid anhydrides was demonstrated by the dual activation using MgBr 2 .OEt 2 . 7 Nevertheless, 2 equiv. of MgBr 2 .OEt 2 and 3 equiv.…”

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confidence: 99%

Lewis acid catalyzed N-acylation of carbamates and oxazolidinones

Reddy¹,

Mahipal²,

Yaragorla³

2008

Arkivoc

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N-Acylation of amides with acid anhydrides by way of dual activation using MgBr2·OEt2

Cited by 28 publications

References 21 publications

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Syntheses of Amino‐Substituted Iridabenzofurans and Subsequent Selective N‐Functionalisation

Reactivity of Phosphonothioamidates with Acid Chlorides and Primary Amines: Synthesis and Conformational Study of N-Acylated Phosphonothioamidates and Phosphonoamidines

Lewis acid catalyzed N-acylation of carbamates and oxazolidinones

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