- Synthesis and antimicrobial activity of phosphonopeptide derivatives incorporating single and dual inhibitors
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In diagnostic microbiology, culture media are widely used for detection of pathogenic bacteria. Such media employ various ingredients to optimize detection of specific pathogens such as chromogenic enzyme substrates and selective inhibitors to reduce the presence of commensal bacteria. Despite this, it is rarely possible to inhibit the growth of all commensal bacteria, and thus pathogens can be overgrown and remain undetected. One approach to attempt to remedy this is the use of “suicide substrates” that can target specific bacterial enzymes and selectively inhibit unwanted bacterial species. With the purpose of identifying novel selective inhibitors, six novel phosphonopeptide derivatives based on D/L-fosfalin and β-chloro-L-alanine were synthesized and tested on 19 different strains of clinically relevant bacteria. Several compounds show potential as useful selective agents that could be exploited in the recovery of several bacterial pathogens including Salmonella, Pseudomonas aeruginosa, and Listeria.
- Anderson, Rosaleen J.,Gray, Mark,Marrs, Emma C. L.,Ng, Keng Tiong,Orenga, Sylvain,Perry, John D.
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supporting information
(2020/04/10)
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- 1-(Acylamino)alkylphosphonic acids—alkaline deacylation
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The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O?)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O?)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.
- Cypryk, Marek,Drabowicz, Jozef,Gostynski, Bartlomiej,Kudzin, Marcin H.,Kudzin, Zbigniew H,Urbaniak, Pawel
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- 1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions
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The 1-(N-acylamino)alkylphosphonic acids (AC)-AAP belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AAP on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media. In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AAP, including 1-(N-acetylamino)alkyl-phosphonic Ac-AAP, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AAP, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AAP, and 1-(N-benzoylamino)-alkylphosphonic Bz-AAP, derived from representative 1-aminoalkylphosphonic acids AAP (GlyP, AlaP, ValP, PglP, and PheP) in neutral and 2?M HCl solutions.
- Cypryk, Marek,Drabowicz, Jozef,Gostynski, Bartlomiej,Kudzin, Marcin H.,Kudzin, Zbigniew H.,Urbaniak, Pawel
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p. 651 - 658
(2017/06/05)
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- Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
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A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.
- Qian, Renzhe,Horak, Jeannie,Hammerschmidt, Friedrich
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p. 737 - 744
(2017/06/05)
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- Tritylamine (triphenylmethylamine) in organic synthesis; III. The synthesis of 1-aminoalkylphosphonic acids in the reaction of N-(triphenylmethyl) alkanimines with phosphorus trichloride in acetic acid or with phosphonic (phosphorous) acid in acetic anhydride
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The reaction of phosphorus trichloride in acetic acid or phosphonic (phosphorous) acid in acetic anhydride, with N-(triphenylmethyl)alkanimines gives 1-acetylaminoalkylphosphonic acids 1a-j, which after hydrolysis give 1-aminoalkylphosphonic acids 2a-j in good yields. ARKAT USA, Inc.
- Goldeman, Waldemar,Soroka, Miroslaw
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experimental part
p. 360 - 369
(2011/02/27)
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- POLYMERIZABLE PHOSPHONIC ACID DERIVATIVE AND ADHESIVE COMPOSITION COMPRISING THE SAME
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The present invention provides an adhesive composition comprising a polymerizable phosphonic acid derivative which is a composition having intramolecularly a polymerizable group and a phosphonic acid group, represented by the general formula [1]: wherein R represents a polymerizable group;A represents an oxygen atom or a sulfur atom;Xqs represent independently an oxygen atom or a sulfur atom;Yqs represent independently the same or different organic group;Zqs may be independently the same or different from each other and, a part of the Zqs optionally selected or all of the Zqs represent organic groups having a substituent which is an organic group other than a polymerizable group and a phosphonic acid group;p is an integer from 1 to 10;q is an integer from 1 to p; when p is 1, q is 1;X1 represents an oxygen atom or a sulfur atom;Y1 represents an organic group;Z1 represents an organic group having one or more of substituents which are organic groups other than an acidic group and a polymerizable group, or a salt thereof. The adhesive composition or the salt thereof according to the present invention improve a shelf life and adhesion properties of an adhesive composition comprising essentially a (meth)acrylate monomer having intramolecularly an acidic group and water in dental treatment.
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Page/Page column 6-7
(2009/03/07)
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- Application of silicon-phosphorus based reagents in synthesis of aminophosphonates. Part 2: Reactions of N-(Triphenylmethyl)-aldimines with the silylated phosphorus acid esters
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Reactions of silylated phosphorus acid esters with N-triphenylmethylaldimines (N-tritylaldimines) were investigated. N-Tritylmethaneimine reacts at room temperature with a mixture of P(OMe)3 and Me3SiBr forming the corresponding aminophosphonate derivatives in high yield. Other N-tritylimines are resistant toward the silylated reagents at room temperature, but undergo a similar phosphorylation reaction at elevated temperatures to form the expected aminophosphonic acids.
- Boduszek,Soroka
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p. 1105 - 1111
(2007/10/03)
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- The formation of α-amino- and α-hydroxy-alkanephosphonic acids in the reactions of phosphite esters with aldehydes and alkyl carbamates
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The preparation of α-aminoalkanephosphonic acids from triphenyl phosphite, an aldehyde, and ethyl or benzyl carbamate in glacial acetic acid, followed by hydrolysis, is accompanied by the formation of the corresponding α-hydroxyphosphonic acid. Reaction in toluene, using boron trifluoride-etherate as catalyst, affords an alternative preparative procedure but does not prevent the formation of α-hydroxyphosphonic acid. 31P nmr reveals the presence of numerous intermediates. The reactions are discussed.
- Hudson, Harry R.,Ismail, Fatima,Pianka, Max,Wan, Chi-Wai
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p. 245 - 257
(2007/10/03)
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- Preparation of 1-aminoalkylphosphonic acids and 2-aminoalkylphosphonic acids by reductive amination of oxoalkylphosphonates
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By reacting dialkyl 1-oxo- or 2-oxoalkylphosphonates with benzhydrylamine followed by reduction with triacetoxyborohydride and acid hydrolysis gave corresponding aminoalkylphosphonic acids with satisfactory yields. The use of benzylamine, α-methylbenzylamine and tritylamine was unsuccessful in the case of dialkyl 1-oxoalkylphosphonates whereas conversion of 2-oxoalkylphosphonates was also achieved although with lower yields.
- Ryglowski, Artur,Kafarski, Pawel
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p. 10685 - 10692
(2007/10/03)
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- A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds
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A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.
- Demir, Ayhan S.,Tanyeli, Cihangir,Sesenoglu, Oezge,Demic, Serafettin,Evin, Oezden Oezel
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p. 407 - 410
(2007/10/02)
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- ORGANOPHOSPHORUS COMPOUNDS AS POTENTIAL FUNGICIDES. PART II. AMINOALKANE-, GUANIDINOALKANE-, AND THIOUREIDOALKANE-PHOSPHONIC ACIDS: PREPARATION, SPECTROSCOPY, AND FUNGICIDAL ACTIVITY
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A range of α-amino-, ω-amino-, α-guanidino-, and ω-guanidinoalkanephosphonic acids has been prepared for the purpose of studying their spectroscopic features and fungicidal activity.In addition, α-thioureido-octanephosphonic acid and thioureylene-1,1-bis(1-octanephosphonic acid) were isolated during the preparation of α-guanidino-octanephosphonic acid. 31P, 1H, and 13C nmr spectral data which were obtained for solutions of the amino- and guanidino-compounds in D2O or D2O/D2SO4, and for the thioureido compounds in DMSO-d6, are discussed together with previouslyreported data for the aminophosphonic types.FAB mass spectrometry generally gives strong pseudomolecular ions + for the zwitterionic amino- and guanidino-compounds with relatively simple fragmentations.Fungicidal activity of the α-aminophosphonic acids was found to be greater than for the ω-amino compounds, with maximum activity at a chain length of three carbon atoms when used as a seed dressing for the control of Drechslera spp.Moderately good activity was shown by the thioureido compounds against a number of fungal organisms in vitro but the guanidino-compounds exhibited low activity.Key words: Organophosphorus; fungicides; aminophosphonic acids; guanidinophosphonic acids; NMR spectroscopy; FAB mass spectroscopy.
- Cameron, David G.,Hudson, Harry R.,Pianka, Max
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- SYNTHESIS OF DERIVATIVES OF 1-AMINOETHYLPHOSPHONIC AND 1-AMINOETHYLPHOSPHINIC ACIDS AS SUBSTRATES FOR PENICILLINACYLASES
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Racemic and optically active N-phenylacetyl derivatives of 1-aminoethylphosphonic acid, 1-aminoethylphosphinic acid, and their mono- and diesters have been synthesized to study the substrate specificity of penicillinacylases.
- Solodenko, V. A.,Kasheva, T. N.,Mironenko, D. A.,Kozlova, E. V.,Shvyadas, V. K.,Kukhar, V. P.
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p. 1209 - 1215
(2007/10/02)
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- A PRACTICAL SYNTHESIS OF α-AMINOPHOSPHONIC ACIDS
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The preparation of diterbutyl-N (diphenylmethylene) aminomethylphosphonate 3 in four steps (42percent overall yield) from N-hydroxymethyl phthalimide 1 is described.Various α substituted α-aminophosphonic acids 5 containing functionalized unsaturated chains have been synthesized by alkylation of 3 under phase transfer catalysis with halides, Michael acceptors and palladium promoted reactions, followed by mild hydrolysis. Key words: Schiff bases of diterbutylaminomethylphosphonate; phase transfer catalysis; palladium-catalyzed allylic substitution; Michael additions.
- Genet, J. P.,Uziel, J.,Port, M.,Touzin, A. M.,Roland, S.,et al.
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- Preparation of optically active 1-aminoalkylphosphonic acids by stereoselective enzymatic hydrolysis of racemic N-acylated 1-aminoalkylphosphonic acids
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N-Phenylacetylated derivatives of 1-aminoalkylphosphonic acids were synthesized and high enantioselectivity of their hydrolysis by penicillin acylase (EC 3.5.1.11) was demonstrated. Stereoselective enzymatic hydrolysis of racemic 1-(N-phenylacetylamino) alkylphosphonic acids was used for preparation of enantiomeric 1-aminoalkylphosphonic acids. The kinetic regularities of penicillin acylase catalyzed hydrolysis were established and the biocatalytic process was optimized to increase the optical purity and the yield of the optically active product.
- Solodenko,Kasheva,Kukhar,Kozlova,Mironenko,Svedas,Belozersky
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p. 3989 - 3998
(2007/10/02)
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- THE SYNTHESIS OF CYCLOPHOSPHONODIPEPTIDES
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Dipeptides and cyclodipeptides containing aminoalkyl phosphonyl groups have been synthesized.The geometric isomers of some of them are separated and the molecular structures are confirmed by NMR, IR, MS or X-ray diffraction.
- Chen, Ru-Yu,Dan, Shi-Cain
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- Process for the preparation of α-aminoalkylphosphonic acids and of α-aminoalkylphosphinic acids
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α-Aminoalkylphosphonic and α-aminoalkylphosphinic acids of the formula I STR1 where n=1 or 0, R1 =H, CH3 or CH2 --C6 H5 R2 =H (for n=1) and also=alkyl or phenyl (for n=0) are prepared by Hofmann deradation from compounds of the formula II STR2 wherein n and R1 have the same meaning as in formula I, R3 =alkyl (for n=1), alkyl or phenyl (for n=0), and Mp+ =p-valent cation, with subsequent working up in the known manner. Some of the compounds I are biologically active, and some are intermediates for the preparation of biologically active compounds.
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- Synthesis of 1-Aminoalkylphosphonic Acids via Amidoalkylation of Phosphorous Acid by N,N'-Alkylidenbisamides
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N,N'-Alkylidenebisamides 1, totally unsuitable as amidoalkylating agents toward phosphorous acid, react with its "activated" form prepared "in situ" from phosphorous(III) chloride and acetic acid to give the desired 1-amidoalkylphosphonic acids 2 in high yield.
- Soroka, Miroslaw,Jaworska, Dorota,Szczesny, Zbigniew
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p. 1153 - 1155
(2007/10/02)
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- The Synthesis of 1-Aminoalkylphosphonic Acids. A Revised Mechanism of the Reaction of Phosphorus Trichloride, Amides and Aldehydes or Ketones in Acetic Acid (Oleksyszyn Reaction)
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The mechanism of the amidoalkylation of trivalent phosphorus compounds in acetic acid has been reinvestigated.Evidence is presented that 1-(acylamino)alkyl acetates 5 and not N,N'-alkylidenebisamides 2 are the intermediates in this reaction.Supporting literature analogies are discussed.This paper also describes a convenient procedure for the preparation of crude (acylamino)alkyl alkanoates 5, which are excellent amidoalkylating agents.The usefulness of these reagents is demonstrated by a simple two-step "one pot" synthesis of 1-aminoalkylphosphinic acids 1.
- Soroka, Miroslaw
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p. 331 - 334
(2007/10/02)
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- 1-Aminoalkanephosphonic acids. Addition of diethyl phosphite to N-diisobutylaluminio-aldimines
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A new route to 1-aminoalkanephosphonic acids starting from nitriles has been elaborated.The nitriles are reduced by Dibal-H into imine derivatives; addition with diethyl phosphite gives the corresponding 1-aminoalkanephosphonates.Hydrolysis of latter compounds gives the 1-aminoalkanephosphonic acids.
- Kudzin, Zbigniew H.,Majchrzak, Michal W.
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p. 245 - 248
(2007/10/02)
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- An Amidoalkylation of Trivalent Phosphorus Compounds with P(O)H Functions Including Acetic Acid Solutions of PCl3, RPCl2 or R2PCl, Diesters of Phosphorous Acid and Phosphorus-III-Acids
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An amidoalkylation of PCl3 or its organic derivatives in acetic acid solution takes place because equilibrium between AcOH and >P-Cl exist, leading to hydroxychlorophosphines.Those last compounds undergo an amidoalkylation like other nucleophiles.Based on these data, it was shown that an amidoalkylation reaction is usual for all phosphorus compounds with the R2P(O)H system and provides derivatives with the >N-C-P(O)R2 functions.The scope and limitation of these reactions are discussed.
- Oleksyszyn, Jozef
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- CONVERSION OF AMINO ACIDS AND DIPEPTIDES INTO THEIR PHOSPHONIC ANALOGS; Aminoalkylphosphonic acids and peptides II.
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Acylamino carboxylic acids were degradated by the Hunsdiecker-reaction; the bromo-derivatives were reacted with NaPO(OC2H5)2.Aminophosphonic acids were obtained by acidic hydrolysis, and half-blocked derivatives by the selective removal of masking substituents.Two phosphonopeptides were also prepared by this route.
- Oesapay, George,Szilagyi, Ildiko,Seres, Jenoe
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p. 2977 - 2984
(2007/10/02)
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- 1-Aminoalkylphosphonous Acids. Part 1. Isosteres of the Protein Amino Acids
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The synthesis of 1-aminoalkylphosphonous acids, isosteres of the protein amino acids, by addition of hypophosphorous acid to diphenylmethylimines is described.These analogues of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tyrosine, tryptophan, serine, threonine, methionine, cysteine, cystine, glutamic acid, lysine, ornithine, arginine, and proline have been prepared and the analogues of alanine, valine, leucine, phenylalanine, and methionine resolved.The alanine, valine and methionine analogues have interesting antimicrobial activity and the alanine analogue has plant growth inhibiting properties.Oxidation of the appropriate 1-aminoalkylphosphonous acids gave the 1-aminoalkylphosphonic acid analogues of (+/-)-alanine, (-)-alanine, (+/-)-valine, (-)-valine, (+/-)-serine, (+/-)-threonine, (+/-)-lysine, (-)-leucine, and (+/-)-ornithine.
- Baylis, E. Keith,Campbell, Colin D.,Dingwall, John G.
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p. 2845 - 2853
(2007/10/02)
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- Chemical process for the production of α-aminophosphonic acids and peptide derivatives
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The present invention provides a process for the production of physiologically-useful α-aminophosphonic acids and peptide derivatives of the formula: STR1 wherein R and R1 may be the same or different and each can be hydrogen, deuterium or an optionally substituted lower alkyl group, lower alkenyl, lower alkynyl, cycloalkyl, aryl or heterocyclic radical containing one or more oxygen, nitrogen or sulphur atoms and which may be fused to an aromatic ring, a lower alkyl group substituted by a cycloalkyl radical, a lower alkyl group substituted by an aryl radical, a lower alkyl group substituted by a heterocyclic radical as defined above or R and R1 together form a polymethylene chain optionally interrupted by an oxygen, nitrogen or sulphur atom, or R1 represents, together with the C(R)--N2 can be hydrogen, optionally substituted lower alkyl, cycloalkyl, aryl or lower alkyl substituted by a cycloalkyl radical, lower alkyl substituted by a heterocyclic radical containing one or more nitrogen atoms; by a heterocyclic radical containing one or more nitrogen atoms, or R2 together with the C(H)--N residue to which it is attached, may represent the atoms required to complete a heterocyclic radical; and n is 0, 1, 2, 3 or 4; comprising oxidizing, using an oxidizing agent, a compound having the formula: STR2 wherein R, R1, R2 and n have their previous significance, and Z is H or a protecting group usually used for an amino group; and then removing any protecting group.
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- Synthesis of 1-Aminoalkane Phosphonic Acids via Benzhydrylic Schiff Bases
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A simple synthesis of 1-aminoalkanephosphonic acids is described.The addition of diethylphosphite to alkylidene- and arylidenebenzhydrylamines yields the N-benzhydryl-1-aminoalkanephosphonic acid esters.The title compounds are formed by treatment of the N-blocked esters with hydrobromic acid.The starting amine can be recycled from the hydrylbromide. - Key words: 1-Aminoalkane Phosphonic Acids, Benzhydrylic, Schiff Bases
- Issleib, Kurt,Doepfer, Klaus-Peter,Balszuweit, Arno
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p. 1392 - 1394
(2007/10/02)
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