Catalyst-Free Microwave-Assisted Synthesis of α-Aminophosphonates in a Three-Component System: R1C(O)R2-(EtO)2P(O)H-RNH2

Kabachnik, M. M.; Zobnina, E. V.; Beletskaya, I. P.

doi:10.1055/s-2005-868519

Cited by 63 publications

(27 citation statements)

References 11 publications

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“…In this way, instead of coordinating the tin(II) halide cocatalyst and leading to catalysts of low activities, the nitrogen atom will be protonated by the HCl liberated to form the platinum-hydrido species (8), the 'starting' complex of the catalytic cycle. According to a generally accepted mechanism of platinum-catalyzed hydroformylation, the coordination of the substrate provides the five-coordinated alkene complex (9). The insertion of alkene into the PteH bond results in the formation of the alkyl complex (10).…”

Section: Intermolecular Relations Of Molecular Structure 6b and The Smentioning

confidence: 99%

N-Benzyl and N-aryl bis(phospha-Mannich adducts): Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation

Bálint

Fazekas

Pongrácz

et al. 2012

Journal of Organometallic Chemistry

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Section: Intermolecular Relations Of Molecular Structure 6b and The Smentioning

confidence: 99%

N-Benzyl and N-aryl bis(phospha-Mannich adducts): Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation

Bálint

Fazekas

Pongrácz

et al. 2012

Journal of Organometallic Chemistry

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“…Prolonged treatment of pure 9 with diethyl phosphite and indium chloride in tetrahydrofuran did not furnish 10b. Kabachnik et al showed that microwave acti-vation in the case of hindered ketones gave better results than conventional heating, [33] but in our case it was not helpful. Finally, a Pudovik-type reaction was investigated by using 9 as the starting material.…”

Section: Synthesis Of the α-Phosphonic Analogue Of Aminocitratementioning

confidence: 87%

Aminophosphonic Acids and Aminobis(phosphonic acids) as Potential Inhibitors of Penicillin‐Binding Proteins

et al. 2008

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Aminophosphonic acids and aminobis(phosphonic acids) have been prepared by the alkylation of Schiff bases with methyl bromoacetate or ethyl acrylate. Other pathways, like the modified Pudovik reaction and Kabachnik–Fields reaction, have been considered for the synthesis of the α‐phosphonic bioisoster of aminocitrate. Partial or complete deprotection of the phosphonate ester have been realised by either acidic hydrolysis or by treatment with trimethylsilyl bromide. Evaluation against penicillin‐binding proteins has shown that our compounds are modest inhibitors of class A β‐lactamases, but have an interesting activity against R39 (D,D‐peptidase/carboxypeptidase). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…Typically, a-aminoalkanephosphonates are formed in good yield by treating a carbonyl compound and an amine with a dialkyl phosphite in the presence of an organic base, an alkali metal alkoxide, or a Brønsted/Lewis acid. Recent preparative modifications of the reaction which significantly simplify the original method and increase the yield of the product concern the use of microwave irradiation [44][45][46][47][48][49], silica gel-supported reagents [43,46,49,50], surface-mediated reactions on Al 2 O 3 [51,52], ionic liquids as solvents [53], solvent-free conditions [43,44,47,54,55], and water-tolerant catalysts (magnesium perchlorate [56,57], lithium perchlorate [58,59], metal triflates [60][61][62], indium trichloride [63], samarium diiodide [64], lanthanide trichloride [65], TaCl 5 /SiO 2 [66], bismuth nitrate pentahydrate [67], scandium tris (dodecyl sulfate) [68], tetrabromomethane [54], and montmorillonite KSF [69]). …”

Section: Amidoalkylation In the Carbonyl Compound-amine-phosphite Thrmentioning

confidence: 99%

Chemistry of Aminophosphonic Acids and Phosphonopeptides

Kukhar

Romanenko

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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Aminophosphonic (and aminophosphinic) acids occupy a prominent position in the understanding of bioprocesses in living organisms and in the construction of new bioregulators -pharmaceuticals and agrochemicals. The so-called phosphorus analogs of the amino acids, aminophosphonic and aminophosphinic acids, are amino acid mimetics in which the carboxylic group is substituted by a phosphonic acid residue P(O)(OH) 2 or phosphinic acid group P(O)(OH)R. The replacement of the carboxylic group by a phosphonic or related moiety results in a number of important consequences: the central atom of a phosphonic acid function consists of an additional substituent that has a tetrahedral configuration in contrast to the planar carbonyl atom of carboxylic group. There are also significant differences in the acidity and steric bulk of these residues. The tetrahedral configuration of the pentavalent phosphorus atom mimics the transition state of the peptide bond cleavage reaction in some enzyme-substrate interactions that is used in the synthesis of new inhibitors. The hydrolytic stability of CÀP bonds is often used in order to prepare stable analogs of bioactive phosphates OÀP(O)(OH) 2 . In addition, aminophosphonic acids and their derivatives are important as metal-complexing agents, which have diagnostic and therapeutic applications, and as industrial chemicals in water treatment, metal extraction, or pollution control.Synthesis, and the chemical, physical, and biological properties of aminophosphonic acids and some directions for their practical application are presented in a number of reviews and book chapters. The most comprehensive account of the chemistry and biology of aminophosphonates and aminophosphinate which covers literature up to 2000 is presented in Kukhar and Hudson ([1] and references therein). Readers are referred to this reference for more detailed information concerning specific aspects of the chemistry and biological activity of aminophosphonic acid derivatives. The purpose of this chapter is to give an updated report on aminophosphonic acids as analogs of amino acids. Numerous heterocyclic compounds that contain both phosphonic and amino groups will not be covered in this report.

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Catalyst-Free Microwave-Assisted Synthesis of α-Aminophosphonates in a Three-Component System: R¹C(O)R²-(EtO)₂P(O)H-RNH₂

Abstract: An effective catalyst-free microwave-assisted synthesis of a-aminophosphonates from ketones in a three-component system was shown. The method affords a-aminophosphonates in high yields from various ketones including natural porphyrine derivatives.

Cited by 63 publications

References 11 publications

N-Benzyl and N-aryl bis(phospha-Mannich adducts): Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation

N-Benzyl and N-aryl bis(phospha-Mannich adducts): Synthesis and catalytic activity of the related bidentate chelate platinum complexes in hydroformylation

Aminophosphonic Acids and Aminobis(phosphonic acids) as Potential Inhibitors of Penicillin‐Binding Proteins

Chemistry of Aminophosphonic Acids and Phosphonopeptides

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