94068-22-1Relevant academic research and scientific papers
Acyloxy derivatives of trivalent phosphorus in amidoalkylation of hydrophosphoryl compounds
Dmitriev,Ragulin
, p. 1888 - 1894 (2013)
In order to model the previously suggested mechanism of the P-C bond formation via the Arbuzov reaction, we have studied the interaction of diethylacylphosphite (prepared beforehand as well as generated in situ from tetraethylpyrophosphite) with the in situ generated acyliminium cation. Various conditions of in situ generation of acylphosphite derivatives of P(III) from hydrophosphoryl compounds and acyliminium ions from N,N′- alkylidenebiscarbamates have been investigated: solvent nature, acid catalyst, and the reagents mixing order). The results obtained have confirmed the suggested mechanism of three-component reaction of amidoalkylation of hydrophosphoryl compounds with the formation of P-C bond via the Arbuzov reaction of in situ formed intermediates.
Synthesis of Phosphinic Analogue of Alanylleucine
Dmitriev, M. E.,Golovash, S. R.,Grigorkevich, O. S.,Ragulin, V. V.,Tsebrikova, G. S.
, p. 753 - 756 (2020/07/02)
Abstract: The amidoalkylation reactions of a phosphonous acid containing a structural isostere of leucine in acetyl chloride and(or) acetic anhydride were studied under conditions of acid catalysis. A two-component method for the synthesis of a phosphinic
Amidoalkylation of hydrophosphoryl compounds
Dmitriev,Rossinets,Ragulin
experimental part, p. 1092 - 1104 (2011/10/17)
A new mild procedure of the amidoalkylation of hydrophosphoryl compounds in a mixture of acetic anhydride and acetyl chloride was developed as a convenient method of constructing the a-aminophosphoryl fragment of the pseudo-a,a'-dipeptide molecule. The reaction intermediates N,N'-benzylidene- and N,N'-alkylidenebiscarbamates were detected, isolated, and identified. The report presents the results of studying the direct interaction of hydrophosphoryl compounds previously synthesized with biscarbamates in acetic anhydride and other solvents, the influence of the structure of phosphorus component and biscarbamate, and the effect of acid catalysis on the course of this two-component reaction. A new version of the mechanism of the three-component reaction of amidoalkylation of hydrophosphoryl compounds is suggested: it is regarded as a multistage process involving the stage of biscarbamate formation followed by the stage of Arbuzov-type reaction with the intermediate formation of acyliminium cation and P-OAc derivative with trivalent phosphorus. Pleiades Publishing, Ltd., 2011.
Synthesis of 1-Aminoalkylphosphonic Acids via Amidoalkylation of Phosphorous Acid by N,N'-Alkylidenbisamides
Soroka, Miroslaw,Jaworska, Dorota,Szczesny, Zbigniew
, p. 1153 - 1155 (2007/10/02)
N,N'-Alkylidenebisamides 1, totally unsuitable as amidoalkylating agents toward phosphorous acid, react with its "activated" form prepared "in situ" from phosphorous(III) chloride and acetic acid to give the desired 1-amidoalkylphosphonic acids 2 in high yield.
Some Applications of the Curtius Rearrangement
Moutevelis-Minakakis, Panagiota,Photaki, Iphigenia
, p. 2277 - 2282 (2007/10/02)
Pairs of optically pure enantiomers of substituted 1,1-diamines have been prepared from the azides of L-amino-acids via the Curtius rearrangement.This synthesis is based on the interchange of two groups attached to the asymmetrically substituted tetrahedr
