6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction

Bálint, Erika; Tripolszky, Anna; Tajti, Ádám

doi:10.1515/9783110535839-006

Cited by 16 publications

(11 citation statements)

References 78 publications

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“…Both reaction types were performed in the presence of a catalyst and/or a solvent. [14] Nowadays, greener accomplishments have come to the front, from which the catalyst-and solventfree microwave (MW)-assisted variations are to be mentioned. [14][15][16][17][18] The benzhydryl group may be utilized as an N-protecting group in organic and peptide chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…[14] Nowadays, greener accomplishments have come to the front, from which the catalyst-and solventfree microwave (MW)-assisted variations are to be mentioned. [14][15][16][17][18] The benzhydryl group may be utilized as an N-protecting group in organic and peptide chemistry. [19][20][21] The easy introduction and elimination of this moiety, as well as the stability and the good crystallization properties of the products make this unit useful for preparative chemists.…”

Section: Introductionmentioning

confidence: 99%

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Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Hudson

Tajti

Bálint

et al. 2020

Synthetic Communications

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A series of N-benzhydryl protected a-aminophosphonates with a-phenyl, a-(1-naphtyl), a-(9-anthryl) or a-(1-pyrenyl) substituents was synthesized by the Kabachnik-Fields condensation of diphenylmethylamine (benzhydrylamine), the corresponding aryl aldehyde and a dialkyl phosphite under MW irradiation. X-ray studies performed at low temperatures for a few of these a-aminophosphonates confirmed the presence of unusually short intramolecular C a-H dþ ÁÁÁ dþ H-C peri contacts.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Hudson

Tajti

Bálint

et al. 2020

Synthetic Communications

Self Cite

View full text Add to dashboard Cite

show abstract

“…Over the seven decades from its discovery, several exotic catalysts and/or solvents have been tried out in the Kabachnik–Fields reaction [13,14]. However, in most cases, catalyst-free and often solvent-free approaches could be performed applying the microwave (MW) technique [9,13,15,16,17,18].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component

et al. 2019

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In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-αaminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,NBis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik–Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.

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“…Phosphonic analogues of phenylglycine were reported to exhibit their interesting herbicidal activity [20,21], and are used as plant growth regulators [20,21] or agrochemical fungicides [20,21]. Therefore, methods for their preparation are still intensively developed [22].…”

Section: Introductionmentioning

confidence: 99%

The Effect of New Thiophene-Derived Diphenyl Aminophosphonates on Growth of Terrestrial Plants

et al. 2019

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The aim of this work was to evaluate the impact of the thiophene-derived aminophosphonates 1–6 on seedling emergence and growth of monocotyledonous oat (Avena sativa) and dicotyledonous radish (Raphanus sativus L.), and phytotoxicity against three persistent and resistant weeds (Galinsoga parviflora Cav., Rumex acetosa L., and Chenopodium album). Aminophosphonates 1–6 have never been described in the literature. The phytotoxicity of tested aminophosphonates toward their potential application as soil-applied herbicides was evaluated according to the OECD (Organization for Economic and Cooperation Development Publishing) 208 Guideline. In addition, their ecotoxicological impact on crustaceans Heterocypris incongruens and bacteria Aliivibrio fischeri was measured using the OSTRACODTOXKITTM and Microtox® tests. Obtained results showed that none of the tested compounds were found sufficiently phytotoxic and none of them have any herbicidal potential. None of the tested compounds showed important toxicity against Aliivibrio fischeri but they should be considered as slightly harmful. Harmful impacts of compounds 1–6 on Heterocypris incongruens were found to be significant.

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6. Synthesis of α-aminophosphonates by the Kabachnik–Fields reaction and by the Pudovik reaction

Cited by 16 publications

References 78 publications

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Microwave-assisted synthesis of α-aminophosphonates with sterically demanding α-aryl substituents

Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component

The Effect of New Thiophene-Derived Diphenyl Aminophosphonates on Growth of Terrestrial Plants

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