M. N. Dimukhametov, V. F. Mironov, D. R. Islamov, I. A. Litvinov, O. I. Gnezdilov, Yu. V. Danilova, “Reaction of sodium <i>N</i>-benzylideneglycinate with dialkyl chlorophosphites in the presence of water”, Mendeleev Commun., 2021, Volume 31, Issue 1,Pages <nobr>107

Communications

Reaction of sodium N-benzylideneglycinate with dialkyl chlorophosphites in the presence of water

M. N. Dimukhametov^a, V. F. Mironov^a, D. R. Islamov^a, I. A. Litvinov^a, O. I. Gnezdilov^b, Yu. V. Danilova^c

^a A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^b E.K. Zavoisky Physical-Technical Institute, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russian Federation
^c Kazan National Research Technological University, Kazan, Russian Federation

Abstract: The outcome of reaction of sodium N-benzylideneglycinate containing water in its crystal lattice with dialkyl chlorophosphites depends on the mode of addition of the latter. Upon the simultaneous mixing of the reactants, 1,4-bis[α-(dialkoxyphosphoryl)benzyl]piperazine-2,5-diones are formed from two molecules of each reactant. With the slow addition of dialkyl chlorophosphite, the main reaction product is 2-{3-[α-(dialkoxyphosphoryl)benzyl]-5-oxo-2-phenylimidazolidin-1-yl}acetic acid (‘1: 2 adduct’), its formation comprising 1,4-migration of dialkoxyphosphoryl moiety.

Keywords: sodium N-benzylideneglycinate, dialkyl chlorophosphite, 5-oxo-2-phenylimidazolidine, piperazine-2,5-dione, 1-aminophosphonate, diversity-oriented synthesis.

Language: English

DOI: 10.1016/j.mencom.2021.01.033

	*Supplementary materials:*
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