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Onys’ko, P. P.; Kim, T. V.; Kiseleva, E. I.; Sinitsa, A. D.

doi:10.1023/a:1012310329462

Cited by 12 publications

(26 citation statements)

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“…To avoid possible 1,3-prototropic rearrangements, [26,27] phenyl and p-anisyl groups were used as substituents at the nitrogen atom. The p-anisyl protective group can be removed by the action of cerium ammonium nitrate; this procedure is well established and used in the chemistry of aminophosphonic acids.…”

Section: Resultsmentioning

confidence: 99%

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

et al. 2008

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Section: Resultsmentioning

confidence: 99%

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

et al. 2008

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“…For the construction of heterocycles it is possible to use an azaallyl fragment, an azomethine bond, or a 1,3-heterodiene system. The presence of an activating phosphorus group in arylideneaminophosphonates gives rise to the possibility of a 1,2H-shift and the generation of azomethine ylides, which readily form mono-and bicyclic derivatives of phosphorylated pyrrolidines during reaction with dipolarophiles [118][119][120]. The stereoselectivity of cycloaddition depends on the method of generation of the azomethine ylides.…”

Section: Nitrogen-containing Heterocycles Based On Phosphorylated Imimentioning

confidence: 99%

“…The stereoselectivity of cycloaddition depends on the method of generation of the azomethine ylides. The simultaneous presence of activating (COOR) and nucleofugic (Br) substituents in the dipolarophile makes it possible to obtain condensed three-and four-membered nitrogen-containing heterocycles with fragments of aminophosphonic and aminocarboxylic acids [119,120].…”

Section: Nitrogen-containing Heterocycles Based On Phosphorylated Imimentioning

confidence: 99%

“…The cyclization of imines with -mercaptocarboxylic acids at the C=N bond opens up the way to derivatives of thiazolidones with a phosphoryl group [121][122][123][124]. Syntheses of the functionalized heterodienes used in the production of five-and six-membered heterocycles as a result of [4+1] and [4+2] cycloaddition reactions were realized.…”

Section: Nitrogen-containing Heterocycles Based On Phosphorylated Imimentioning

confidence: 99%

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Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine (Review)

Lozinskii

Il'chenko

2009

Chem Heterocycl Comp

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“…Despite the fact that CF 3 is a much stronger than phenyl, compounds If and Ih isomerizes much more easily than Ie and Ig. Here, evidently, 1,3-H transfer is favored by the formation of the favorable N-benzylidene structure in compounds IVe and IVh [1,4,7,8]. Unlike N-benzyltrifluoroacetimidoylphosphonates If and Ih, compounds Ia3Ie, Ig, Ii, and Ij in the absense of bases either do not izomerize at all or isomerize partially with attendant side processes.…”

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Sigmatropic Isomerizations in Azaallyl Systems: XXII. 1,3-Proton Transfer in (N-Alkyltrifluoroacetimidoyl)phosphonates

et al. 2005

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The reaction of N-alkyltrifluoroacetimidoyl chlorides with trialkyl phosphites leads to corresponding imidoylphosphonates CF 3 C[P(O)(OAlk) 2 ]=NCH 2 R. These compounds undergo irreversible 1,3-H shift catalyzed by nitrogenous bases to give phosphorylated imines CF 3 CH[P(O)(OAlk) 2 ]N=CHR. The tendency for prototropism increases with increasing electronegativity of substituents R: CF 3 > CH 2 OMe > H > Me. N-Cyclopentyl analogs of the obtained compounds show no tendency for prototropism. Imidoylphosphonates exist mainly as Z isomers [Z/E~(6310) : 1].Imidoylphosphonates are promising synthetic precursors of biologically important derivatives of a-aminophosphonic acids. As they are the [oxidized] form of a-aminophosphonates, reduction of the C=N bond (conversion PC=N 6 PCHN) is a way of their transformation into a-aminophosphoryl derivarives.Intramolecular proton transfer that simulates biochemical transamination allows this process to be performed in the absence of a foreign reducing agent. In previous communications of this series we showed that 1,3-H transfer is characteristic of benz-[2] and some alkanimidoylphosphonates [1]. In the present ÄÄÄÄÄÄÄÄÄÄÄÄ work we synthesized (N-alkyltrifluoroacetimidoyl)-phosphonates I and considered the effect of substituents in the N-alkyl radical on the 1,3-H transfer. The electron-acceptor and simultaneously fairly chemically inert trifluoromethyl group on the sp 2 -carbon atom of compound I favors proton transfer and thus allows synthesis of phosphorus analogs of trifluoroalanine that act as enzyme inhibitors [1,3].Imidoylphosphonates I were prepared by reaction of trialkyl phosphites with imidoyl chlorides II obtained by chlorination of trifluoroacetamides III (Scheme 1). Scheme 1. ; = o ; = g O R CF 3 N R`7 76 X 2 PCl 3 ; o ; = g O R CF 3 R`7 76 I N (AlkO) 3 P ; CF 3 I g

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Cited by 12 publications

References 1 publication

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

Catalytic Hydrogenation of α‐Iminophosphonates as a Method for the Synthesis of Racemic and Optically Active α‐Aminophosphonates

Chemistry of heterocyclic compounds at the Institute of Organic Chemistry, National Academy of Sciences of Ukraine (Review)

Sigmatropic Isomerizations in Azaallyl Systems: XXII. 1,3-Proton Transfer in (N-Alkyltrifluoroacetimidoyl)phosphonates

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