Synthesis and rearrangements of N-trichloroacetylfluoroacetimidoyl chloride and its phosphorylation products

Rassukana, Yuliya V.; Davydova, Kateryna O.; Onys’ko, P. P.; Sinitsa, A. D.

doi:10.1016/s0022-1139(02)00160-4

Cited by 21 publications

(19 citation statements)

References 6 publications

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“…Yield 40%, bp 132oC (0.08 mm Hg). 1 Compounds Va3Vd and Vf3Vi. A mixture of equimolar amounts of imidoyl chloride and ethyl diphenylphosphinite IVb or a 10% excess of triethyl phosphite IVa was heated until gas evolution began.…”

Section: Methodsmentioning

confidence: 99%

“…Imidoylphosphonate Va, the simplest derivative of N-alkylbenzimidoylphosphonates, too, is prone to prototropy neither on thermolysis (120oC, without solvent) nor under conditions of base catalysis (EtONa, EtOH, reflux). It is only after prolonged heating in triethylamine that small amounts (<5%) of isomer VIa (R = R`= H, R``= EtO) (d CHP 4.9 ppm, d; 2 J HP 18 Hz) and its transformation product could be detected by 1 …”

Section: äääääääääääämentioning

confidence: 99%

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Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates

et al. 2004

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Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N!C triad were revealed and applied in the synthesis of =-aminophosphonic acid derivatives.Imidoylphosphonates containing a-hydrogen atoms in the N-alkyl group are potential 1,3-prototropic systems. Prototropy the phosphorylated C=N3C 1,3-prototropic triad presents both theoretical and practical interest. The A 76 47 B interconversion can be regarded as a [phosphorus] model of the biochemical transamination reaction in living bodies.The 1,3-prototropic shift in the phosphorylated azaallyl triad makes evident genetic relation between derivatives of imidoylphosphonic (A) and a-aminoalkylphosphonic acids (B) that attract increased interest in view of their biological activity [2, 3].Transformations like A 6 B belong to fundamental properties of imidoylphosphonates and form an important method for preparing a-aminoalkylphosphoryl derivatives [4].In previous communications of this series we showed that the phosphorus-containing group controls facility and direction of prototropic migrations in the C=N3C triad. In detail it was established [4,5] that N-benzylbenzimidoylphosphoryl derivatives I under mild conditions, even in the absence of bases, undergo an irreversible 1,3-prototropic shift to form Nbenzylidene-a-aminoalkylphosphoryl derivatives II (Scheme 1).To assess the effect of the N-alkyl substituent on the prototropy in the C3N3C triad, in the present work ÄÄÄÄÄÄÄÄÄÄÄÄ 1 For communication XIX, see [1]. Scheme 1.; C 9 0 P ; 9 0 P = T

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Section: Methodsmentioning

confidence: 99%

Section: äääääääääääämentioning

confidence: 99%

Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates

et al. 2004

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“…Additionally, the addition of phosphites to iminophosphonate esters has been studied. This reaction is limited to specific substrates, and usually the obtained bisphosphonates 53 are unstable, and phosphoryl C-N transfer to compounds 54 is observed (Scheme 26), which may be considered an example of an aza-Perkov reaction [121][122][123]. A specific and unexpected reaction was the addition of silylated dialkyl phosphites to 4-phosphono-1-aza-1,3-dienes 50, which resulted in γ-phosphono-α-aminobisphosphonates 51 (Scheme 25) [120].…”

Section: Miscellaneous Proceduresmentioning

confidence: 99%

Synthetic Procedures Leading towards Aminobisphosphonates

Chmielewska

Kafarski

2016

Molecules

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Abstract:Growing interest in the biological activity of aminobisphosphonates has stimulated the development of methods for their synthesis. Although several general procedures were previously elaborated to reach this goal, aminobisphosphonate chemistry is still developing quite substantially. Thus, innovative modifications of the existing commonly used reactions, as well as development of new procedures, are presented in this review, concentrating on recent achievements. Additionally, selected examples of aminobisphosphonate derivatization illustrate their usefulness for obtaining new diagnostic and therapeutic agents.

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“…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. By such a method it is possible to obtain oxazaphospholines [125][126][127][128][129][130][131][132][133], phosphorylated oxadiazines [134], dihydrooxazines and dihydrooxazoles [133][134][135] The high reactivity of activated iminocarboxylates makes it possible to use these systems for the aminoalkylation of electron-rich heterocycles. Functionalized indoles containing fragments of trifluoroalanine, in particular, were synthesized by this method [136].…”

Section: Nitrogen-containing Heterocycles Based On Phosphorylated Imimentioning

confidence: 99%

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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Synthesis and rearrangements of N-trichloroacetylfluoroacetimidoyl chloride and its phosphorylation products

Cited by 21 publications

References 6 publications

Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates

Sigmatropic isomerizations in azaallyl systems: XX. N-Alkylbenzimidoylphosphonates

Synthetic Procedures Leading towards Aminobisphosphonates

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

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