Al(OTf)₃ as an Efficient Catalyst for One-Pot Synthesis of Primary Diethyl 1-Aminophosphonates Under Solvent-Free Conditions

REFERENCES

• Horiguchi , M. ; Kandatsu , M. Isolation of 2-aminoethanephosphonic acid from rumen protozoa . Nature 1959 , 184 , 901 – 902 .
   PubMed Web of Science ®Google Scholar
• Allen , M. C. ; Fuhrer , W. ; Tuck , B. ; Wade , R. ; Wood , J. M. Renin inhibitors: Synthesis of transition-state analogue inhibitors containing phosphorus acid derivatives at the scissile bond . J. Med. Chem. 1989 , 32 , 1652 – 1661 .
   PubMed Web of Science ®Google Scholar
• Logusch , E. W. ; Walker , D. M. ; McDonald , J. F. ; Leo , G. C. ; Grang , J. E. Synthesis α- and γ-alkyl-substituted phosphinothricins: Potent new inhibitors of glutamine synthetase . J. Org. Chem. 1988 , 53 , 4069 – 4074 .
   Web of Science ®Google Scholar
• Giannousis , P. P. ; Bartlett , P. A. Phosphorus amino-acid-analogs as inhibitors of leucine aminopeptidase . J. Med. Chem. 1987 , 30 , 1603 – 1609 .
   PubMed Web of Science ®Google Scholar
• Hoagland , R. E. Naturally occurring carbon-phosphorus compounds as herbicides . ACS Sym. Ser. 1988 , 380 , 182 – 210 .
   Google Scholar
• Emsle , J. ; Hall , E. D. The Chemistry of Phosphorus ; Harper and Row : London , 1976 .
   Google Scholar
• Danila , C. D. ; Wang , X. ; Hubble , H. ; Antipin , I. S. ; Pinkhassik , E. Increasing permeability of phospholipid bilayer membranes to alanine with synthetic α-aminophosphonate carriers . Bioorg. Med. Chem. Lett. 2008 , 18 , 2320 – 2323 .
   PubMed Web of Science ®Google Scholar
• Lejczak , B. ; Kafarski , P. ; Sztajer , H. ; Mastalerz , P. Antibacterial activity of phosphono dipeptides related to alafosfalin . J. Med. Chem. 1986 , 29 , 2212 – 2217 .
   PubMed Web of Science ®Google Scholar
• Kukhar , V. P. ; Solodenko , N. M. ; Solodenko , V. A. Biological activity of the phosphorus analogs of amino-acids . Biokhim. Zh. 1988 , 60 , 95 – 111 .
   PubMed Web of Science ®Google Scholar
• Bhagat , S. ; Chakraborti , A. K. An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik–Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate . J. Org. Chem. 2007 , 7 , 1263 – 1270 .
   Web of Science ®Google Scholar
• Zahouily , M. ; Elmakssoudi , A. ; Mezdar , A. ; Rayadh , A. ; Sebti , S. Natural phosphate and potassium fluoride doped natural phosphate catalyzed simple one-pot synthesis of α-amino phosphonates under solvent-free conditions at room temperature . Catal. Commun. 2007 , 8 , 225 – 230 .
   Web of Science ®Google Scholar
• Heydari , A. ; Hamadi , H. ; Pourayoubi , M. A new one-pot synthesis of α-amino phosphonates catalyzed by H3PW12O40 . Catal. Commun. 2007 , 8 , 1224 – 1226 .
   Web of Science ®Google Scholar
• Bhattacharya , A. K. ; Kaur , T. An efficient one-pot synthesis of α-amino phosphonates catalyzed by bismuth nitrate pentahydrate . Synlett. 2007 , 5 , 745 – 748 .
   Web of Science ®Google Scholar
• Ambica , K. S. ; Taneja , S. C. ; Hundal , M. S. ; Kapoor , K. K. One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina . Tetrahedron Lett. 2008 , 49 , 2208 – 2212 .
   Web of Science ®Google Scholar
• Ollevier , T. ; Nadeau , E. ; Guay-Begin , A. A. Direct-type catalytic three-component Mannick reaction in aqueous media . Tetrahedron Lett. 2006 , 47 , 8351 – 8354 .
   Web of Science ®Google Scholar
• Chalmers , M. E. ; Kosolapoff , G. M. The synthesis of amino-substituted phosphonic acids . J. Am. Chem. Soc. 1953 , 75 , 5278 – 5280 .
   Web of Science ®Google Scholar
• Takahashi , H. ; Yoshioka , M. ; Imai , N. ; Onimura , K. ; Kobayashi , S. Simple and improved preparation of α-aminophosphonic acid derivatives, key building blocks of phosphonopeptides. Synthesis 1994, 763–764.
   Web of Science ®Google Scholar
• Matveeva , E. D. ; Podrugina , T. A. ; Tishkovskaya , E. V. ; Tomilova , L. G. ; Zefirov , N. S. A novel catalytic three-component synthesis (Kabachnick–Fields reaction) of α-aminophosphonates from ketones . Synlett 2003 , 15 , 2321 – 2324 .
   Web of Science ®Google Scholar
• Kaboudin , B. ; Nazari , R. Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions . Tetrahedron Lett. 2001 , 42 , 8211 – 8213 .
   Web of Science ®Google Scholar
• Kaboudin , B. Surface-mediated solid phase reactions: A simple and new method for the synthesis of α-aminophosphonates under solvent-free conditions . Chem. Lett. 2001 , 30 , 880 – 881 .
   Web of Science ®Google Scholar
• Kaboudin , B. ; Saadati , F. Studies on the synthesis of 1-aminoalkylphosphonates from aldehydes using silica-supported ammonium hydrogen carbonate . Synthesis 2004 , 8 , 1249 – 1252 .
   Web of Science ®Google Scholar
• Kaboudin , B. ; Rahmani , A. Silica-supported ammonium hydrogen carbonate as an efficient reagent for one-pot synthesis of 1-aminophosphonates from aldehydes . Synthesis 2003 , 17 , 2705 – 2708 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. A high yielding preparation of alpha-trimethylsilyloxyphosphonates by silylation of alpha-hydroxyphosphonates with HMDS catalyzed by iodine . Tetrahedron Lett. 2002 , 43 , 3653 – 3655 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. Preparation of alpha-ketophosphonates by oxidation of alpha-hydroxyphosphonates with neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions and potassium permanganate in dry benzene . Tetrahedron Lett. 2002 , 43 , 477 – 480 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. PPh3/DDQ as a neutral systemfor the facile preparation of diethyl α-bromo, α-iodo and α-azidophosphonates from diethyl α-hydroxyphosphonates . Tetrahedron 2004 , 45 , 203 – 210 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. ; Ghassamipour , S. Aluminium triflate [Al(OTf)3] as a recyclable catalyst for the conversion of alpha-hydroxyphosphonates, alcohols and phenols to their corresponding O-silylated products with hexamethyldisilazane (HMDS) . Synthesis 2005 , 595 – 599 .
   Web of Science ®Google Scholar
• Firouzabadi , H. ; Iranpoor , N. ; Sobhani , S. Metal triflates-catalyzed one-pot synthesis of α-aminophosphonates from carbonyl compounds in the absence of solvent . Synthesis 2004 , 2692 – 2696 .
   Web of Science ®Google Scholar