Al(H2PO4)3 as an Efficient and Reusable Catalyst for One‐pot Three‐component Synthesis of α‐Amino Phosphonates under Solvent‐free Conditions

Synthesis of α-amino phosphonates is described under solvent-free conditions at 100°C from reaction between aldehydes and amines in the presence of trialkyl phosphites using Al(H2PO4)3 as an efficient and reusable heterogeneous catalyst. The advantages of this procedure are short reaction time, flexibility and having high to excellent yields.

[1]  A. Heydari,et al.  Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates , 2009 .

[2]  H. Shaterian,et al.  Environmentally Friendly Preparation of 3,4-Dihydropyrimidin-2(1H)-thiones Catalyzed by Al(H2PO4)3 , 2008 .

[3]  A. Heydari,et al.  Organocatalytic synthesis of a-hydroxy and a-aminophosphonates , 2008 .

[4]  H. Shaterian,et al.  Environmentally Friendly Preparation of Amidoalkyl Naphthols , 2008 .

[5]  H. Shaterian,et al.  An efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) catalyzed by aluminum tris(dihydrogen phosphate) under solvent-free and ambient conditions , 2008 .

[6]  M. Hosseini‐Sarvari.  TiO2 as a new and reusable catalyst for one-pot three-component syntheses of α-aminophosphonates in solvent-free conditions , 2008 .

[7]  P. Wadgaonkar,et al.  Sulfamic acid: An efficient and cost-effective solid acid catalyst for the synthesis of α-aminophosphonates at ambient temperature , 2008 .

[8]  A. Bhattacharya,et al.  Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot , 2008 .

[9]  M. Kar,et al.  Al(H2PO4)3: An efficient catalyst for nitration of organic compounds with nitric acid , 2008 .

[10]  A. Heydari,et al.  Coupling of Aldehydes, Amines, and Trimethyl Phosphite Promoted by Amberlyst-15: Highly Efficient Synthesis of α-Aminophosphonates , 2008 .

[11]  A. Heydari,et al.  A new one-pot synthesis of α-amino phosphonates catalyzed by H3PW12O40 , 2007 .

[12]  A. Heydari,et al.  One-pot three-component synthesis of a-amino phosphonate derivatives , 2007 .

[13]  Asit K Chakraborti,et al.  An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of alpha-aminophosphonates catalyzed by magnesium perchlorate. , 2007, The Journal of organic chemistry.

[14]  Jie Wu,et al.  A Highly Efficient Catalyst FeCl3 in the Synthesis of α‐Amino Phosphonates via Three‐component Reactions , 2006 .

[15]  Wei Zhang,et al.  Microwave-assisted solvent-free and catalyst-free Kabachnik–Fields reactions for α-amino phosphonates , 2006 .

[16]  N. Iranpoor,et al.  Metal Triflate-Catalyzed One-Pot Synthesis of α-Aminophosphonates from Carbonyl Compounds in the Absence of Solvent , 2004 .

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

[18]  T. Akiyama,et al.  Brønsted Acid-Mediated Synthesis of α-Amino Phosphonates under Solvent-Free Conditions , 2003 .

[19]  J. Yadav,et al.  An eco-friendly approach for the synthesis of α-aminophosphonates using ionic liquids , 2002 .

[20]  N. Azizi,et al.  A New Protocol for a One-pot Synthesis of α-Amino Phosphonates by Reaction of Imines Prepared In Situ with Trialkylphosphites , 2002 .

[21]  S. Chandrasekhar,et al.  Three component coupling catalyzed by TaCl5–SiO2: synthesis of α-amino phosphonates , 2001 .

[22]  Shuj Kobayashi,et al.  Facile synthesis of α-amino phosphonates in water using a Lewis acid–surfactant-combined catalyst , 2000 .

[23]  P. Bartlett,et al.  MACROCYCLIC INHIBITORS OF PENICILLOPEPSIN. 1. DESIGN, SYNTHESIS, AND EVALUATION OF AN INHIBITOR BRIDGED BETWEEN P1 AND P3 , 1998 .

[24]  S. Shibuya,et al.  Stereoselective Synthesis of .beta.-Oxygenated .alpha.-Hydroxyphosphonates by Lewis Acid-Mediated Stereoselective Hydrophosphonylation of .alpha.-Benzyloxy Aldehydes. An Application to the Synthesis of Phosphonic Acid Analogs of Oxyamino Acids , 1994 .

[25]  W. Stahl,et al.  Non-peptide-based inhibitors of human immunodeficiency virus-1 protease , 1994 .

[26]  S. Benkovic,et al.  Peptide bond formation via catalytic antibodies: Synthesis of a novel phosphonate diester hapten , 1994 .

[27]  S. Benkovic,et al.  Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids. , 1994, Science.

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

[29]  S. Laschat,et al.  Carbohydrates as Chiral Templates: Stereoselective Synthesis of (R)- and (S)-α-Aminophosphonic Acid Derivatives , 1992 .

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

[31]  L. Maier,et al.  ORGANIC PHOSPHORUS COMPOUNDS 96.1 RESOLUTION OF 1-AMINO-2-(4-FLUOROPHENYL)ETHYLPHOSPHONIC ACID AS WELL AS SOME DI- AND TRIPEPTIDES , 1991 .

[32]  L. Maier.  ORGANIC PHOSPHORUS COMPOUNDS 91.1 SYNTHESIS AND PROPERTIES OF 1-AMINO-2-ARYLETHYLPHOSPHONIC AND-PHOSPHINIC ACIDS AS WELL AS -PHOSPHINE OXIDES , 1990 .

[33]  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.

[34]  C. Hassall,et al.  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid. , 1986, Journal of medicinal chemistry.