Solvent-Free Synthesis of α-Aminophosphonates from N-Heterocycles, Activated Acetylenes, and Diphenyl Phosphite

REFERENCES

• Thomas , A. A. ; Sharpless , K. B. The catalytic asymmetric aminohydroxylation of unsaturated phosphonates . J. Org. Chem. 1999 , 64 , 8379 – 8385 .
   PubMed Web of Science ®Google Scholar
• Albrecht , S. ; Defoin , A. ; Salomon , E. ; Tarnus , C. ; Wetterholmb , A. ; Haeggstro , J. Z. Synthesis and structure–activity relationships of novel nonpeptidic metallo aminopeptidase inhibitors . Bioorg. Med. Chem. 2006 , 14 , 7241 – 7257 .
   PubMed Web of Science ®Google Scholar
• Joossens , J. ; Veken , P. V. ; Surpateanu , G. ; Anne , A. M. ; El-Sayed , I. ; Ali , O. M. ; Augustyns , K. ; Haemers , A. Diphenyl phosphonate inhibitors for the urokinase-type plasminogen activator: Optimization of the P4 position . J. Med. Chem. 2006 , 49 , 5785 – 5793 .
   PubMed Web of Science ®Google Scholar
• Qi , X. ; Lee , S. H. ; Kwon , J. Y. ; Kim , Y. ; Kim , S. J. ; Lee , Y. S. ; Yoon , J. Aminobromination of unsaturated phosphonates . J. Org. Chem. 2003 , 68 , 9140 – 9143 .
   PubMed Web of Science ®Google Scholar
• Ntai , I. ; Manier , M. L. ; Hachey , D. L. ; Bachmann , B. O. Biosynthetic origins of C-P bond containing tripeptide K-26 . Org. Lett. 2005 , 7 , 2763 – 2765 .
   PubMed Web of Science ®Google Scholar
• Joly , G. D. ; Jacobsen , E. N. Thiourea-catalyzed enantioselective hydrophosphonylation of imines: Practical access to enantiomerically enriched α-amino phosphonic acids . J. Am. Chem. Soc. 2004 , 126 , 4102 – 4103 .
   PubMed Web of Science ®Google Scholar
• Berlicki , L. ; Kafarski , P. Computer-aided analysis and design of phosphonic and phosphinic enzyme inhibitors as potential drugs and agrochemicals . Curr. Org. Chem. 2005 , 9 , 1829 – 1950 .
   Google Scholar
• Azizi , N. ; Saidi , M. R. Synthesis of tertiary α-amino phosphonate by one-pot, three-component coupling mediated by LPDE . Tetrahedron 2003 , 59 , 5329 – 5332 .
   Web of Science ®Google Scholar
• Xu , F. ; Luo , Y. W. J. ; Shen , Q. ; Chen , H. Facile one-pot synthesis of phosphonates using lanthanide chloride as catalyst . Heteroat. Chem. 2006 , 17 , 389 – 392 .
   Web of Science ®Google Scholar
• Bioton , L. D. ; Villemin , D. ; Lohier , J. F. ; Sopkova , J. ; Jaffr , P. A. Synthesis of triazolyl-alkylphosphonate starting from ω-azidoalkylphosphonates or α-alkynylphosphonates . Tetrahedron 2007 , 63 , 9677 – 9684 .
   Google Scholar
• Xu , F. ; Luo , Y. ; Deng , M. ; Shen , Q. One-pot synthesis of α-amino phosphonates using samarium diiodide as a catalyst precursor . Eur. J. Org. Chem. 2003 , 24 , 4728 – 4730 .
   Web of Science ®Google Scholar
• Vanderhoydonck , B. ; Stevens , C. V. Conjugate addition to 1-phosphono-2-aza-1,3-butadienes: Synthesis of phosphonylated γ-lactams . J. Org. Chem. 2005 , 70 , 191 – 198 .
   PubMed Web of Science ®Google Scholar
• Atherton , F. R. ; Hassal , C. H. ; Lambert , R. W. Synthesis and structure–activity relationships of antibacterial phosphonopeptides incorporating (l-aminoethy1)phosphonic acid and (aminomethy1)phosphonic acid . J. Med. Chem. 1986 , 29 , 29 – 40 .
   PubMed Web of Science ®Google Scholar
• Dillinger , H. J. ; Fengler , G. ; Schumann , D. ; Winterfeldt , E. Additionen an die dreifachbindung—XXII: Das thermodynamisch kontrollierte addukt aus tert.butylisonitril und acetylendicarbonester . Tetrahedron 1974 , 30 , 2561 – 2564 .
   Web of Science ®Google Scholar
• Yavari , I. ; Moradi , L. ; Mokhtarporiani-Sanandej , A. ; Mirzaei , A. Efficient synthesis of trialkyl 3-phenylbuta-1,3-diene-1,2,4-tricarboxylates by a novel one-pot multicomponent reaction . Helv. Chim. Acta 2006 , 90 , 392 – 394 .
   Google Scholar
• Yavari , I. ; Zabarjad-Shiraz , N. ; Partovi , T. Stereoselective synthesis of new phosphorylated N,N′-dimethylbarbituric acids. Synth. Commun. 2002, 32, 2763–2769.
   Web of Science ®Google Scholar
• Yavari , I. ; Sabbaghan , M. A synthesis of functionalized pyrroles by reaction of 3,4-diacetylhexane-2,5-dione with primary amines in water . Synth. Commun. 2007 , 37 , 1791 – 1800 .
   Web of Science ®Google Scholar
• Yavari , I. ; Mirzaei , A. ; Moradi , L. ; Mokhtarporiani-Sanandej , A. Efficient synthesis of trialkyl (E)-3-[3-oxo-2–3,4-dihydro-2-(1H)-quinoxalinylidene]-prop-1-ene-1,2,3 tricarboxylates . Synth. Commun. 2007 , 37 , 1195 – 1200 .
   Web of Science ®Google Scholar