A simple protocol for the synthesis of α-substituted phosphonates

GRAPHICAL ABSTRACT ABSTRACT An efficient, easy-to-handle, and mild substitution reaction approach has been developed for the synthesis of phosphonate derivatives, which are very important in the field of industrial, agricultural, and medicinal chemistry. A large number of nucleophiles, including arylamines, alkylamines, heteroarylamines, primary amines and secondary amines, sulfides, and carbides were attempted to react with α-tosyloxyphosphonate 1. The reaction proceeded under catalyst-free and neat conditions and the corresponding phosphonates 2 were afforded in good yields.

[1]  R. Yousefi,et al.  Synthesis of new α-aminophosphonate derivatives incorporating benzimidazole, theophylline and adenine nucleobases using L-cysteine functionalized magnetic nanoparticles (LCMNP) as magnetic reusable catalyst: evaluation of their anticancer properties , 2016 .

[2]  P. V. G. Reddy,et al.  Efficient solvent free synthesis of tertiary α-aminophosphonates using H2Ti3O7 nanotubes as a reusable solid-acid catalyst , 2015 .

[3]  C. Suresh Reddy,et al.  PAA-SIO2 Catalyzed Synthesis, Uv Absorption, and Fluorescence Emission Studies of Diethyl (Aryl/Hetero Aryl Amino)(Pyren-1-Yl)Methylphosphonates , 2015 .

[4]  D. Kowalczyk,et al.  An organocatalytic biomimetic approach to α-aminophosphonates. , 2015, Chemical communications.

[5]  H. Eshghi,et al.  Benzimidazolium dicationic ionic liquid as an efficient and reusable catalyst for the synthesis of α-aminophosphonates and bis (α-aminophosphonates) under solvent-free condition , 2015 .

[6]  Kiran B. Dhopte,et al.  Graphene Oxide as Recyclable Catalyst for One-Pot Synthesis of α-Aminophosphonates , 2015 .

[7]  C. S. Reddy,et al.  Efficient Synthesis of α-Aminophosphonates and Evaluation of Significance of P˭O Group towards Antioxidant Activity , 2015 .

[8]  N. Zefirov,et al.  Immobilized Phthalocyanine Aluminum Complexes in Synthesis of α–Aminophosphonates. Phosphorylation of Various Imines , 2015 .

[9]  I. El-Sayed,et al.  Transition metal complexes of α-aminophosphonates Part I: synthesis, spectroscopic characterization, and in vitro anticancer activity of copper(II) complexes of α-aminophosphonates , 2015, Medicinal Chemistry Research.

[10]  Jianguo Yang,et al.  Synthesis of α-Amino Phosphonates under a Neat Condition Catalyzed by Multiple-Acidic Ionic Liquids , 2014 .

[11]  Qiu Wang,et al.  α-Amination of Phosphonates: A Direct Synthesis of α-Amino Phosphonic Acids and Their Derivatives , 2014 .

[12]  C. N. Raju,et al.  CeCl3·7H2O Catalyzed, Microwave-Assisted High-Yield Synthesis of α-Aminophosphonates and their Biological Studies , 2014 .

[13]  D. She,et al.  Synthesis and Application of N-Tosyl Piperidinyl-Containing α-Aminophosphonates , 2013 .

[14]  D. Rao,et al.  Microwave Assisted Synthesis of Biologically Active α-Aminophosphonates Catalyzed by Nano-BF3·SiO2 under Solvent-Free Conditions , 2013 .

[15]  H. Shaterian,et al.  Nano-TiO2: An Eco-Friendly and Clean Reusable Heterogeneous Catalyst for Preparation of α-Aminophosphonates Under Ambient and Solvent-Free Conditions , 2013 .

[16]  G. El‐Hiti,et al.  Synthesis of a Series of Diphenyl (Arylamino)(Pyridin-3-yl)Methylphosphonates as Potential Antimicrobial Agents , 2013 .

[17]  N. B. Reddy,et al.  Synthesis and Bioassay of Ethyl-2- (2-((Diethoxyphosphoryl) (Aryl) Methylamino)Thiazol-4-Yl)-2-(Methoxyimino)Acetates , 2013 .

[18]  M. Maghsoodlou,et al.  One-Pot, Three-Component Synthesis of α-Amino Phosphonates Using NaHSO4-SiO2 as an Efficient and Reusable Catalyst , 2012 .

[19]  Yufen Zhao,et al.  Copper (I) Iodide-Catalyzed Solvent-Free Synthesis of α-Aminophosphonates , 2011 .

[20]  K. Zomorodian,et al.  Design, Synthesis, and Antifungal Activity of New α-Aminophosphonates , 2011, International journal of medicinal chemistry.

[21]  V. K. Rao,et al.  Synthesis, Antimicrobial, and Antioxidant Activity of New α-Aminophosphonates , 2011 .

[22]  M. Maghsoodlou,et al.  A Novel and Efficient Synthesis of α-Aminophosphonates by Use of Triphenyl Phosphite in Acetic Acid Media , 2011 .

[23]  J. Frère,et al.  Mercaptophosphonate compounds as broad-spectrum inhibitors of the metallo-beta-lactamases. , 2010, Journal of medicinal chemistry.

[24]  M. Shingare,et al.  An Efficient Synthesis and Antibacterial Screening of Novel Oxazepine α-Aminophosphonates by Ultrasound Approach , 2009 .

[25]  A. Ghaderi,et al.  Design and one-pot synthesis of alpha-aminophosphonates and bis(alpha-aminophosphonates) by iron(III) chloride and cytotoxic activity. , 2009, European journal of medicinal chemistry.

[26]  S. Sobhani,et al.  Al(OTf)3 as an Efficient Catalyst for One-Pot Synthesis of Primary Diethyl 1-Aminophosphonates Under Solvent-Free Conditions , 2008 .

[27]  De-Qing Shi,et al.  A Convenient Synthesis and Herbicidal Activity of N-phosphonoalkylpyrazolo[4,3-e][1,2,4]-triazolo[1,5-d]pyrimidines , 2008 .

[28]  A. Chakraborti,et al.  Zirconium(IV) compounds as efficient catalysts for synthesis of alpha-aminophosphonates. , 2008, The Journal of organic chemistry.

[29]  M. Shingare,et al.  Simple and High Yielding Synthesis of New α-Aminophosphonates from Imines , 2008 .

[30]  Ambica,et al.  One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina , 2008 .

[31]  T. Gajda,et al.  Convenient Synthesis of Dialkyl 1‐Azidoalkylphosphonates using Tetramethylguanidinium Azide as Azidation Agent , 2008 .

[32]  M. Xia,et al.  Ultrasound-assisted one-pot approach to alpha-amino phosphonates under solvent-free and catalyst-free conditions. , 2007, Ultrasonics sonochemistry.

[33]  Pradeep Kumar Rajput,et al.  TiCl4-Catalyzed Efficient One-Pot Synthesis of α α-Amino Phosphonates , 2007 .

[34]  N. Zefirov,et al.  Amino acids in a three-component synthesis of α-aminophosphonates derivatives , 2006 .

[35]  Fan Xu,et al.  Facile one‐pot synthesis of α‐amino phosphonates using lanthanide chloride as catalyst , 2006 .

[36]  Zhuang-Ping Zhan,et al.  Bismuth(III) Chloride–Catalyzed Three‐Component Coupling: Synthesis of α‐Amino Phosphonates , 2005 .

[37]  R. Matsubara,et al.  Catalytic Asymmetric Synthesis of α-Amino Phosphonates Using Enantioselective Carbon−Carbon Bond-Forming Reactions , 2004 .

[38]  A. Chakraborty,et al.  In(OTf)3 catalysed simple one-pot synthesis of α-amino phosphonates , 2004 .

[39]  A. Manjula,et al.  One-Pot Synthesis of α-Aminophosphonates: An Inexpensive Approach , 2003 .

[40]  E. Årstad,et al.  Reactions of diethyl mesyl- or tosyloxyphosphonates with diethyl phosphite and base: a method claimed to yield bisphosphonates , 2002 .

[41]  C. Song,et al.  Microwave-assisted Kabachnik-Fields reaction in ionic liquid , 2002 .

[42]  B. Ranu,et al.  General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst , 1999 .

[43]  M. Burk,et al.  Enantioselective Synthesis of α-Hydroxy and α-Amino Phosphonates via Catalytic Asymmetric Hydrogenation , 1999 .

[44]  钱长涛,et al.  One-pot synthesis of α-amino phosphonates from aldehydes using lanthanide triflate as a catalyst , 1998 .

[45]  G. Hägele,et al.  SYNTHESE VON FLUORIERTEN N-ARYLAMINO-ARYLMETHANPHOSPHONSÄUREDIALKYLESTERN , 1994 .

[46]  H. Ha,et al.  An Efficient Synthesis of Anilinobenzylphosphonates , 1992 .

[47]  Paweł Kafarski,et al.  BIOLOGICAL ACTIVITY OF AMINOPHOSPHONIC ACIDS , 1991 .

[48]  J. Wood,et al.  Renin inhibitors. Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond. , 1989, Journal of medicinal chemistry.