4-Phosphoranylidene-5(4H)-oxazolones ? A novel synthesis and properties

Mazurkiewicz, Roman; Pierwocha, A. W.

doi:10.1007/bf00807402

Cited by 25 publications

(17 citation statements)

References 10 publications

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“…11,12 The method consists in the transformation of N-acylated glycine into the corresponding 5(4H)-oxazolone 6 followed by the phosphorylation of this compound in situ with dibromotriphenylphosphorane or dibromotributylphosphorane in the presence of triethylamine (Scheme 2). …”

Section: Methodsmentioning

confidence: 99%

α-Amino acid derivatives with a Cα-P bond in organic synthesis

Mazurkiewicz¹,

Kuźnik²,

Grymel³

et al. 2007

Arkivoc

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α-Amino acid derivatives with a C α -P bond have been used for a wide range of chemical transformations, including synthesis of many kinds of bioactive compounds, e.g. nonproteinogenic α-amino acids, α,β-dehydro-α-amino acids, dehydropeptides, β-lactam antibiotics and glycopeptides. The present review is focused on methods of synthesis of the title compounds, their properties and application in organic synthesis.

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Section: Methodsmentioning

confidence: 99%

α-Amino acid derivatives with a Cα-P bond in organic synthesis

Mazurkiewicz¹,

Kuźnik²,

Grymel³

et al. 2007

Arkivoc

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“…1-(N-Acylamino)alkyltriphenylphosphonium salts 6 were synthesized as described in our previous paper. [11][12][13][14][15] General Procedures for Reaction of 1-(N-acylamino) alkyltriphenylphosphonium Salts 6 with Nucleophiles Procedure A. Reactions were carried out in a glass vial sealed with a screw-cap.…”

Section: Experimental Generalmentioning

confidence: 99%

“…[11][12][13][14][15] In this paper, we describe the application of 1-(N-acylamino)alkyltriphenylphosphonium salts 6 as new versatile and effective amidoalkylating reagents for the α-amidoalkylation of a variety of nucleophiles (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Amidoalkylating Properties of 1-(N-Acylamino)Alkyltriphenylphosphonium Salts

Październiok-Holewa

Adámek

Mazurkiewicz

et al. 2013

Phosphorus, Sulfur, and Silicon and the Related Elements

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Easily accessible 1-(N-acylamino)alkyltriphenylphosphonium salts react smoothly with nitrogen, sulfur, phosphorus and oxygen nucleophiles in the presence of (i-Pr) 2 EtN to give the expected α-amidoalkylation products, usually in good or very good yields. α-Amidoalkylation of dialkyl malonates or acetylacetates requires the application of a much stronger base (DBU) and gives the best results under the influence of microwave irradiation. α-Amidoalkylation of enamines was carried out successfully in the presence of (i-Pr) 2 EtN in a microwave reactor. 1-(N-Acylamino)alkyltriphenylphosphonium salts can be considered as new, convenient and effective α-amidoalkylation agents.

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“…The 1-(N-acylamino)alkyltriphenylphosphonium salts 3 and the 1-(Npivaloylamino)vinyltriphenylphosphonium iodide 5 were synthesized as described in the literature. 11,12 Synthesis of N-Acylaminoalkanephosphonic Acid Esters 4a-c: (Procedure A)…”

Section: -Aminoalkanephosphonic Acid Derivativesmentioning

confidence: 99%

“…One of the most important approaches to 1-aminoalkanephosphonic acids consists in the Michaelis-Arbuzov reaction of trialkyl phosphites with amidoalkylating agents. 1,[4][5][6][7][8][9] Recently, we described simple and effective syntheses of 1-(N-acylamino)alkyltriphenylphosphonium salts 3 10,11 from easily accessible 4-phosphoranylidene-5(4H)-oxazolones 1 12 or their alkylation products 2 13 (Scheme 1). The obtained phosphonium salts are stable, crystalline compounds and can be prepared on kilogram scale using these procedures.…”

Section: Introductionmentioning

confidence: 99%