Synthesis of α‐aminophosphinates by the hydrophosphinylation of imines

Szabó, Ágnes; Petneházy, Imre; Jászay, Zsuzsa M.

doi:10.1002/hc.10133

Cited by 24 publications

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References 9 publications

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“…The synthetic potential of the method has been covered in a series of reviews [27,42,95]. During the last 10 years, direct hydrophosphonylation of imines has been widely used for the preparation of multifunctional a-aminophosphonic acids without the excessive use of protective groups [96][97][98][99][100][101][102][103]. Trialkyl phosphites were evaluated for addition reactions to a,b-unsaturated imines.…”

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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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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Schiff Bases as Inspirational Motif for the Production of Ni(II) and Pd(II) Coordination and Novel Non‐Symmetric Ni(II)‐POCOP Pincer Complexes

et al. 2021

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The synthesis of Ni(II) and Pd (II) coordination complexes containing Schiff's bases derived from the condensation of 2,4dihydroxybenzaldehyde with 4-chloroaniline (L1) or 3,5-dichloroaniline (L2) is described. The condensation of ligands L1 and L2 with chlorodiisopropylphosphine in the presence of a base produced the corresponding non-symmetric pincer ligands POCOP-1 and POCOP-2 with the unexpected CÀ P bond formation by a hydrophosphorylation of the imine process. The new CÀ P bond formation probably occurring by a Kabachnik-Field mechanism type without the requirement of catalysts or additional reagents. Further treatment of ligands POCOP-1 or POCOP-2 with NiCl 2 afforded the non-symmetric pincer complexes Ni(II)-POCOP-1 and Ni(II)-POCOP-2. The crystal structures of L1, 3, Ni(II)-POCOP-1 and Ni(II)-POCOP-2 were unequivocally determined by single crystal X-ray diffraction studies. In addition, the metal complexes were used as catalysts in Suzuki-Miyaura couplings under microwave irradiation, being the Pd(II) derivatives the best catalysts of the series when compared to their Ni(II) analogues under the same reaction conditions.

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