An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate

Bhattacharya, Asish K.; Kaur, Tanpreet

doi:10.1055/s-2007-970762

Cited by 86 publications

(26 citation statements)

References 4 publications

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“…In earlier syntheses, special catalysts (e.g. BiNO 3 [22], phthalocyanine [23], lanthanoid(OTf) 3 [24], magnesium perchlorate [25] and gallium(III) iodide [26]) were applied that cannot be regarded environmentally friendly species. We proved that under MW conditions there was no need for any catalyst.…”

Section: Methodsmentioning

confidence: 99%

“…However, in these cases, the success was limited [68,69,74,75]. The above mentioned resolution methods applying TADDOLand tartaric acid derivatives (22-25) may be regarded efficient as, almost in all instances, at least one of the resolving agents (22)(23)(24)(25) provided the enantiomers of the 5-and 6-membered P-heterocycles (17-21) with an ee above 99%.…”

Section: Scheme 12mentioning

confidence: 99%

“…The optically active aryl-and alkyl-3-phospholene oxides ((R)-or (S)-17a-i) obtained by resolution with TADDOL-or tartaric acid derivatives (22)(23)(24)(25) were also converted to the corresponding optically active borane-and cis-platinum complexes (27* or 28*) (Fig. 1).…”

Section: Complexation Reactions Of Cyclic Phosphines and Bisphosphinesmentioning

confidence: 99%

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Environmentally Friendly Chemistry with Organophosphorus Syntheses in Focus

Keglevich

Grűn²,

Bagi³

et al. 2015

Period. Polytech. Chem. Eng.

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The use of the microwave (MW) Keywords organophosphorus chemistry, green chemistry, microwave, resolution, platinum complexes, dronic acids/dronates IntroductionIn this minireview, our recent results in environmentallyfriendly ("green") chemistry have been summarized. In the first sub-chapter the usefulness of the microwave technique is shown in organophosphorus chemistry. The second sub-chapter summarizes our results on the resolution of cyclic phosphine oxides, as precursors for P-ligands and on the synthesis of platinum complexes as potential catalysts. Catalysts are of utmost importance from the point of view of green chemistry. The last sub-chapter comprises our experiences on the optimization of the synthesis of dronic acid derivatives that are important drugs against bone diseases.

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Section: Methodsmentioning

confidence: 99%

Section: Scheme 12mentioning

confidence: 99%

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Environmentally Friendly Chemistry with Organophosphorus Syntheses in Focus

Keglevich

Grűn²,

Bagi³

et al. 2015

Period. Polytech. Chem. Eng.

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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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“…In contrast to the widespread studies on the one-pot synthesis of secondary and tertiary 1-aminophosphonates [12][13][14][15][16][17], relatively few methods are reported for the one-pot synthesis of primary 1-aminophosphonates. The most typical procedure for the one-pot synthesis of primary 1-aminophosphonates is a Strecker-type reaction [18], which involves the treatment of an aldehyde with ammonia and diethyl phosphite.…”

Section: Introductionmentioning

confidence: 99%