α-Ketiminophosphonates: Synthesis and Applications

REFERENCES

• Kukhar , V. P. and Hadson , H. R. , eds. 2000 . Aminophosphonic and Aminophopshinic Acids. Chemistry and Biological Activity , Chichester , , UK : John Wiley . For an excellent book see:
   Google Scholar
• Kafarski , P. and Lejczak , B. 2001 . Curr. Med. Chem: Anti-Cancer Agent , 1 : 301 – 312 . For reviews see: (a)
   PubMedGoogle Scholar
• Gambecka , J. and Kafarski , P. 2001 . Mini-Rev. Med. Chem. , 1 : 133 – 144 .
   PubMedGoogle Scholar
• Hirschmann , R. , Smith , A. B. III , Taylor , C. M. , Benkovic , P. A. , Taylor , S. D. , Yager , K. M. , Sprengeler , P. A. and Venkovic , S. J. 1994 . Science , 265 : 234 – 237 .
   PubMed Web of Science ®Google Scholar
• Lejczak , B. , Kafarski , P. , Sztajer , H. and Masterlerz , P. 1986 . J. Med. Chem. , 29 : 2212 – 2217 .
   PubMed Web of Science ®Google Scholar
• Oleksyszyn , J. and Powers , J. C. 1991 . Biochemistry , 30 : 485 – 493 .
   PubMed Web of Science ®Google Scholar
• Bartlett , P. A. , Hanson , J. E. and Giannousis , P. G. 1990 . J. Org. Chem. J. Org. Chem. , 55 : 6268 – 6274 .
   Web of Science ®Google Scholar
• Allen , M. C. , Fuhrer , W. , Tuck , B. , Wade , R. and Wood , J. M. 1989 . J. Med. Chem. , 32 : 1652 – 1661 .
   PubMed Web of Science ®Google Scholar
• Atherton , F. R. , Hassall , C. H. and Lambert , R. W. 1986 . J. Med. Chem. , 29 : 29 – 40 .
   PubMed Web of Science ®Google Scholar
• Smith , W. W. and Bartlett , P. A. 1998 . J. Am. Chem. Soc. , 120 : 4622 – 4628 .
   Web of Science ®Google Scholar
• Bonarska , D. , Kleszczyńska , H. and Sarapuk , J. 2002 . Cell Mol. Biol. Lett. , 7 : 929 – 935 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Vicario , J. and Aparicio , D. 2006 . Eur. J. Org. Chem. , : 2843 – 2850 .
   Web of Science ®Google Scholar
• Brady , W. T. and Shieh , C. H. 1983 . J. Org. Chem. , 48 : 2499 – 2502 .
   Web of Science ®Google Scholar
• Palacios , F. , Ochoa de Retana , A. M. , Pascual , S. and Oyarzabal , J. 2004 . J. Org. Chem. , 69 : 8767 – 8774 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Ochoa de Retana , A. M. , Pascual , S. and Oyarzabal , J. 2002 . Org. Lett. , 4 : 769 – 772 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Aparicio , D. and Vicario , J. 2002 . Eur. J. Org. Chem. , : 4131 – 4136 .
   Google Scholar
• Palacios , F. , Aparicio , D. , Rubiales , G. , Alonso , C. and de los Santos , J. M. 2007 . Tetrahedron , 63 : 523 – 575 . For reviews see: (a)
   Web of Science ®Google Scholar
• Fresneda , P. M. and Molina , P. 2004 . Synlett , : 1 – 17 .
   Web of Science ®Google Scholar
• Barluenga , J. and Palacios , F. 1991 . Org. Prep. Proced. Int. , 23 : 1 – 65 .
   Web of Science ®Google Scholar
• Palacios , F. , Alonso , C. , Rubiales , G. and Villegas , M. 2005 . Tetrahedron , 61 : 2779 – 2794 . For contributions of creation of the C˭N bouble bond by means of this process see: (a)
   Web of Science ®Google Scholar
• Palacios , F. , Alonso , C. , Amezua , P. and Rubiales , G. 2002 . J. Org. Chem. , 67 : 1941 – 1946 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Herrán , E. , Rubiales , G. and Ezpeleta , J. M. 2002 . J. Org. Chem. , 67 : 2131 – 2135 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Vicario , J. and Aparicio , D. 2006 . J. Org. Chem. , 71 : 7690 – 7696 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Ochoa de Retana , A. M. and Alonso , J. M. 2006 . J. Org. Chem. , 71 : 6141 – 6148 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Aparicio , D. , Ochoa de Retana , A. M. , de los Santos , J. M. , Gil , J. I. and Alonso , J. M. 2002 . J. Org. Chem. , 67 : 7283 – 7288 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Ochoa de Retana , A. M. , Gil , J. I. and Lopez de Munain , R. 2002 . Org. Lett. , 4 : 2405 – 2408 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Aparicio , D. , Lopez , Y. , de los Santos , J. M. and Ezpeleta , J. M. 2006 . Tetrahedron , 62 : 1095 – 1101 .
   Web of Science ®Google Scholar
• Palacios , F. , Aparicio , Do. , de los Santos , J. M. and Vicario , J. 2001 . Tetrahedron , 57 : 1961 – 1972 .
   Web of Science ®Google Scholar
• Palacios , F. , Aparicio , D. and de los Santos , J. M. 1996 . Tetrahedron , 52 : 4123 – 4132 .
   Web of Science ®Google Scholar
• Palacios , F. , Ochoa de Retana , A. M. , Oyarzabal , J. , Pascual , S. and Fernandez de Troconiz , G. 2008 . J. Org. Chem. , 73 : 4568 – 4574 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Ochoa de Retana , A. M. , Pascual , S. , Lopez de Munain , R. , Oyarzabal , J. and Ezpeleta , J. M. 2005 . Tetrahedron , 61 : 1087 – 1094 .
   Web of Science ®Google Scholar
• Palacios , F. , Aparicio , D. , Garcia , J. , Vicario , J. and Ezpeleta , J. M. 2001 . Eur. J. Org. Chem. , 66 : 3357 – 3365 .
   Google Scholar
• Breuer , E. , Karaman , R. , Goldblum , A. , Gibson , D. , Leader , H. , Potter , B. V. L. and Cummins , J. H. 1988 . J. Chem. Soc., Perkin Trans. 1 , : 3047 – 3057 .
   Google Scholar
• Kudzin , Z. H. and Kotynski , A. 1980 . Synthesis , : 1028 – 1031 .
   Web of Science ®Google Scholar
• Sekine , M. , Satoh , M. , Yamagata , H. and Hata , T. 1980 . J. Org. Chem. , 45 : 4162 – 4167 .
   Web of Science ®Google Scholar
• Cossio , F. P. , Alonso , C. , Lecea , B. , Ayerbe , M. , Rubiales , G. and Palacios , F. 2006 . J. Org. Chem. , 71 : 2839 – 2847 .
   PubMed Web of Science ®Google Scholar
• Palacios , F. , Herran , E. and Rubiales , G. 1999 . J. Org. Chem. , 64 : 6239 – 6246 .
   Web of Science ®Google Scholar
• “ General procedure for the synthesis of β,γ-unsaturated α-iminophosphonates 4. To a solution of the corresponding azide 1 (2.0 mmol) in CH2Cl2 (10 mL) at 0°C, a 1.0 M solution of trimethylphosphine in toluene (2 mL) was added. The resulting solution was stirred for 30 min. until N2 evolution stopped, which indicates the completion of the reaction, and phosphazene 2 formation and can be monitored by 31P NMR. The corresponding neat β,γ-unsaturated α-ketophosphonate 3 (2.0 mmol) was then added, and the reaction was stirred for an additional 30 min at r.t. The solution was diluted with CH2Cl2 (40 mL) and washed with water (3 × 20 mL), dried over MgSO4, and concentrated under reduced pressure to afford a yellow oily crude that was purified by chromatography (SiO2, AcOEt:pentane 3:1) ” .
   Google Scholar