An alternative approach to 2-amino-phenylphosphonic acid
DOI:
https://doi.org/10.13171/mjc731892812-csukAbstract
2-Amino-phenlyphosphonic acid can easily be prepared in five steps from aniline in 38% over-all yield with a phosphoramidate-aminophosphonate rearrangement reaction as the key-step.ÂReferences
- A. Bessmertnykh, C.M. Douaihy, R. Guilard, Direct Synthesis of Amino-substituted Aromatic Phosphonates via Palladium-catalyzed Coupling of Aromatic Mono- and Dibromides with Diethyl Phosphite, Chem. Lett. 2009, 38, 738-739.
T. Hirao, T. Masunaga, Y. Ohshiro, T. Agawa, A Novel Synthesis of Dialkyl Arene-phosphonates, Synthesis, 1981, 56-57.
- T. Hirao, T. Masunaga, N. Yamada, Y. Ohshiro, T. Agawa, Palladium-Catalyzed New Carbon-Phosphorus Bond Formation, B. Chem. Soc. Jpn. 1982, 55, 909-913.
- X.Y. Lu, Z.J. Ni, Palladium-Catalyzed Synthesis of Allylic and Benzylic Sulfides from the Corresponding Dithiocarbonates, Synthesis, 1987, 66-68.
- X.Y. Lu, J.Y. Zhu, Palladium-Catalyzed Reaction of Aryl Polyfluoroalkanesulfonates with O,O-Dialkyl Phosphonates, Synthesis, 1987, 726-727.
- N. Defacqz, B. de Bueger, R. Touillaux, A. Cordi, J. Marchand-Brynaert, Direct phosphonylation of mono- and dihalogenoanilines, Synthesis, 1999, 1368-1372.
- P. Tavs, F. Korte, Zur Herstellung Aromatischer Phosphonsaureester Aus Arylhalogeniden Und Trialkylphosphiten, Tetrahedron, 1967, 23, 4677-4679.
- T.M. Balthazor, R.C. Grabiak, Nickel-Catalyzed Arbuzov Reaction - Mechanistic Observations, J. Org. Chem. 1980, 45, 5425-5426.
- R.C. Grabiak, J.A. Miles, G.M. Schwenzer, Synthesis of Phosphonic Dichlorides and Correlation of Their P-31 Chemical-Shifts, Phosphorus Sulfur 1980, 9, 197-202.
- P. Tavs, Reaction of Aryl Halides with Trialkyl Phosphites and Dialkyl Benzenephosphonites to Aromatic Phosphonates and Phosphinates by Nickel Salt Catalysed Arylation, Chem. Ber. 1970, 103, 2428-2436.
- J.F. Bunnett, E. Mitchel, C. Galli, The Effect of Ortho Substituents in Srn1 Reactions - Some Synthetic Applications, Tetrahedron 1985, 41, 4119-4132.
- J.B. Plumb, R. Obrycki, C.E. Griffin, Phosphonic Acids and Esters. XVI. Formation of Dialkyl Phenylphosphonates by the Photoinitiated Phenylation of Trialkyl Phosphites1,2, The J. Org. Chem. 1966, 31, 2455-2458.
- G. Yang, J. Chun, H. ArakawaUramoto, X. Wang, M.A. Gawinowicz, K. Zhao, D.W. Landry, Anti-cocaine catalytic antibodies: A synthetic approach to improved antibody diversity, J. Am. Chem. Soc. 1996, 118, 5881-5890.
- Z.E. Golubski, Z. Skrowaczewska, New Synthesis of Cyclic Esters of Phosphonic and Thiophosphonic Acids, Synthesis, 1979, 21-23.
- S. Yasui, M. Fujii, C. Kawano, Y. Nishimura, K. Shioji, A. Ohno, Mechanism of Dediazoniation of Arenediazonium Salts with Triphenylphosphine and Trialkyl Phosphites - Generation of Cation Radicals from Trivalent Phosphorus-Compounds and Their Reactions, J. Chem. Soc. Perkin Trans. 2, 1994, 177-183.
- F. Effenberger, H. Kottmann, Oxidative Phosphonylation of Aromatic-Compounds, Tetrahedron 1985, 41, 4171-4182.
- Y.M. Kargin, E.V. Nikitin, O.V. Parakin, G.V. Romanov, A.N. Pudovik, Electrochemical Synthesis of Organo-Phosphorus Compounds, Phosphorus Sulfur 1980, 8, 55-58.
- H. Kottmann, J. Skarzewski, F. Effenberger, Oxidative Phosphonylation of Aromatics with Ammonium Cerium(Iv) Nitrate, Synthesis 1987, 797-801.
- A.M. Jardine, S.M. Vather, T.A. Modro, Metalation-Induced Migration of Phosphorus from Nitrogen to Carbon, J. Org. Chem. 1988, 53, 3983-3985.
- S. Masson, J.F. SaintClair, A. Dore, M. Saquet, Phosphorothioate-mercaptophosphonate rearrangement: Synthesis of new o-mercaptoaryl- and o-mercaptoheteroaryl phosphonates and their derivatives, Bull. Soc. Chim. Fr. 1996, 133, 951-964.
- S.S. De Silva, P.J. Camp, D.K. Henderson, D.C.R. Henry, H. McNab, P.A. Tasker, P. Wight, Attachment of phosphonate-functionalised azo-dyes to oxide surfaces to give enhanced light and wet fastness, Chem. Commun. 2003, 1702-1703.
- A. Mucha, A. Kunert, J. Grembecka, M. Pawelczak, P. Kafarski, A phosphonamidate containing aromatic N-terminal amino group as inhibitor of leucine aminopeptidase - design, synthesis and stability, Eur. J. Med. Chem. 2006, 41, 768-772.
- Y.C. Kim, S.G. Brown, T.K. Harden, J.L. Boyer, G. Dubyak, B.F. King, G. Burnstock, K.A. Jacobson, Structure-activity relationships of pyridoxal phosphate derivatives as potent and selective antagonists of P2X(1) receptors, J. Med. Chem. 2001, 44, 340-349.
- R. Beugelmans, M. Chbani, Photostimulated S(Rn)1 Reactions on Functionalized Aryl Bromides Enhanced by Kl Addition - Synthetic and Mechanistic Aspects, New J. Chem. 1994, 18, 949-952.
- K. Issleib, R. Vollmer, o-Substituted benzenephosphonic acid diethyl ester and o-amino, o-hydroxy, and o-mercaptophenyl phosphine, Z. Chem. 1978, 18, 451-452.
- F. Hammerschmidt, E. Schneyder, E. Zbiral, Novel synthetic aspects of the phosphonate-phosphate rearrangement. 1. A useful approach to 1,2-propadienyl phosphates, Chem. Ber. 1980, 113, 3891-3897.
- F. Hammerschmidt, E. Zbiral, Novel synthetic aspects of the phosphonate-phosphate-rearrangement. II. Synthesis of enolphosphates from 1-oxoalkanphosphonates and sulfur ylides, Monatsh. Chem. 1980, 111, 1015-1023.
- F. Hammerschmidt, S. Schmidt, The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications. Part 4. Deprotonation of secondary benzylic phosphates. Configurationally stable benzylic carbanions with a diethoxyphosphoryloxy substituent and their rearrangement to optically active tertiary α-hydroxy phosphonates, Chem. Ber. 1996, 129, 1503-1508.
- F. Hammerschmidt, S. Schmidt, The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications. Part 5. On the reaction of sec-butyllithium/TMEDA with symmetrical trialkyl phosphates, Monatsh. Chem. 1997, 128, 1173-1180.
- F. Hammerschmidt, H. Voellenkle, Stereochemistry of the phosphate-phosphonate rearrangement, Liebigs Ann. Chem. 1986, 2053-2064.
- N.V. Kolotilo, A.A. Sinitsa, Y.V. Rassukanaya, P.P. Onys'ko, N-sulfonyl-and N-phosphoryl-benzimidoylphosphonates, Russ. J. Gen. Chem. 2006, 76, 1210-1218.
- A.N. Pudovik, M.G. Zimin, I.V. Konovalova, V.M. Pozhidaev, L.I. Vinogradov, Aminophosphonate-amidophosphate rearrangement of bis(dialkylphosphono)alkylamines, Zh. Obshch. Khim. 1975, 45, 30-37.
- B. Dhawan, D. Redmore, Rearrangement of a di-tert-butyl aryl phosphate to a di-tert-butyl (2-hydroxyaryl)phosphonate. A convenient preparation of (2-hydroxyphenyl)- and (2-hydroxy-5-methoxyphenyl)phosphonic acids, Synth. Commun. 1985, 15, 411-416.
- B. Dhawan, D. Redmore, Rearrangement of di-tert-butyl aryl phosphates to di-tert-butyl (2-hydroxyaryl)phosphonates. Preparation of (2-hydroxy-1,3-phenylene)bisphosphonic acids, Phosphorus, Sulfur Silicon Relat. Elem. 1989, 42, 177-182.
- B. Dhawan, D. Redmore, Metalation-induced 1,3-migration of a diphenylphosphinyl group from oxygen to carbon. Preparation of 2-(diphenylphosphinyl)phenols. J. Chem. Res., Synop.1989, 328.
- E. Kuliszewska, F. Hammerschmidt, On the rearrangement of N-aryl-N-Boc-phosphor-
amidates to N-Boc-protected o-aminoaryl-phosphonates, Monatsh. Chem. 2018, 149, 87-98.
- J.-L. Paparin, A. Amador, E. Badaroux, S. Bot, C. Caillet, T. Convard, D. Da Costa, D. Dukhan, L. Griffe, J.-F. Griffon, M. La Colla, F. Leroy, M. Liuzzi, A.G. Loi, J. McCarville, V. Mascia, J. Milhau, L. Onidi, C. Pierra, R. Rahali, E. Rosinosky, E. Sais, M. Seifer, D. Surleraux, D. Standring, C.B. Dousson, Discovery of benzophosphadiazine drug candidate IDX375: A novel hepatitis C allosteric NS5B RdRp inhibitor, Bioorg. Med. Chem. Lett. 2017, 27, 2634-2640.
- Y. Wang, J. Desai, Y. Zhang, S.R. Malwal, C.J. Shin, X. Feng, H. Sun, G. Liu, R.-T. Guo, E. Oldfield, Bacterial Cell Growth Inhibitors Targeting Undecaprenyl Diphosphate Synthase and Undecaprenyl Diphosphate Phosphatase, ChemMedChem. 2016, 11, 2311-2319.
- W. Dabkowski, J. Michalski, C. Radziejewski, Z. Skrzypczynski, Phosphoric and phosphinic sulfonic anhydrides - reinvestigation and corrections. Novel methods of synthesis, Chem. Ber. 1982, 115, 1636-1643.
- G.O. Doak, L.D. Freedman, Synthesis of phosphanilic acid and related compounds, J. Am. Chem. Soc. 1952, 74, 753-754.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).
