Download PDF
Synthesis 2009(14): 2357-2360  
DOI: 10.1055/s-0029-1216834
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Novel α-Aminophosphonates Containing Adamantyl Fragment

Maria M. Kabachnik*, Lidiya I. Minaeva, Irina P. Beletskaya
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow 119992, Russia
Fax: +7(495)9392221; e-Mail: mariamk@mail.ru;
Further Information

Publication History

Received 12 March 2009
Publication Date:
25 May 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Novel α-aminophosphonates containing an adamantyl fragment were prepared by a microwave-assisted cadmium(II) iodide-catalyzed Kabachnik-Fields reaction.

Key words

multicomponent reaction - aminophosphorylation - adamantane α-aminophosphonates - microwave irradiation

    References

  • For some reviews see:
  • 1a Cherkasov RA. Galkin VI. Russ. Chem. Rev.  1998,  67:  857 
    Search in Google Scholar
  • 1b Kukhar’ VP. Svistunova NYu. Solodenko VA. Soloshonok VA. Russ. Chem. Rev.  1993,  62:  261 
    Search in Google Scholar
  • 1c Uziel J. Genet JP. Zh. Org. Khim.  1997,  23:  1521 ; Chem. Abstr. 1998, 129, 149000
    Search in Google Scholar
  • 1d Ordonez M. Rojas-Cabrera H. Cativiela C. Tetrahedron  2009,  65:  17 
    Search in Google Scholar
  • 2a Kafarski P. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem.  1991,  63:  193 
    Search in Google Scholar
  • 2b Evstigneeva ZG. Solov’eva NA. Sidel’nicova LI. Appl. Biochem. Microbiol.  2003,  39:  539 
    Search in Google Scholar
  • 2c Forlani G. Obojska A. Berlicki L. Kafarski P. J. Agric. Food Chem.  2006,  54:  796 
    Search in Google Scholar
  • 2d Kurtz T. Schulter K. Kaula U. Bergmann B. Walter RD. Geffken D. Bioorg. Med. Chem.  2006,  14:  5121 
    Search in Google Scholar
  • 3 Nehéz M. Fischer GW. Scheufler H. Schmidt R. Sipos T. Dési I. Ecotoxicol. Environ. Saf.  1992,  24:  13 
    CrossrefPubMedSearch in Google Scholar
  • 4a Tripathi R. Mishra D. Rizvi A. Singh C. Life Sci.  2007,  81:  1544 
    Search in Google Scholar
  • 4b Kadi AA. El-Brollosy NR. Al-Deeb OA. Habib EE. Ibrahim TM. El-Emam AA. Eur. J. Med. Chem.  2007,  42:  235 
    Search in Google Scholar
  • 4c Zajdel P. Subra G. Bojarski AJ. Duszyńska B. Tatarczyńska E. Nikiforuk A. Chojnacka-Wójcik E. Pawowski M. Martinez J. Bioorg. Med. Chem.  2007,  15:  2907 
    Search in Google Scholar
  • 5a Stamatiou G. Kolocouris A. Kolocouris N. Fytas G. Foscolos GB. Neyts J. De Clercq E. Bioorg. Med. Chem. Lett.  2001,  11:  2137 
    Search in Google Scholar
  • 5b Stylianakis I. Kolocouris A. Kolocouris N. Fytas G. Foscolos GB. Padalko E. Neyts J. De Clercq E. Bioorg. Med. Chem. Lett.  2003,  13:  1699 
    Search in Google Scholar
  • 6a Burstein ME. Serbin AV. Khakhulina TV. Alymova IV. Stotskaya LL. Bogdan OP. Manukchina EE. Jdanov VV. Sharova NK. Bukrinskaya AG. Antiviral Res.  1999,  41:  135 
    Search in Google Scholar
  • 6b Burstein ME. Serbin AV. Khakhulina TV. Bukrinskaya AG. Antiviral Res.  2000,  46:  44 
    Search in Google Scholar
  • 6c Kesel AJ. Bioorg. Med. Chem.  2003,  11:  4599 
    Search in Google Scholar
  • 6d Balzarini J. Orzeszko B. Maurin JK. Orzeszko A. Eur. J. Med. Chem.  2007,  42:  993 
    Search in Google Scholar
  • 6e Zoidis G. Papanastasiou I. Dotsikas I. Sandova A. Dos Santos RIG. Papadopoulou-Daifoti Z. Vamvakides A. Kolocourisa N. Felix R. Bioorg. Med. Chem.  2005,  13:  2791 
    Search in Google Scholar
  • 7a Webster SP. Ward P. Binnie C. Craigie E. McConnell KMM. Sooy K. Vinter A. Seckl JR. Walker BR. Bioorg. Med. Chem. Lett.  2007,  17:  2838 
    Search in Google Scholar
  • 7b Baxter A. Bent J. Bowers K. Braddock M. Brough S. Fagura M. Lawson M. McInally T. Mortimore M. Robertson M. Weaver R. Webborn P. Bioorg. Med. Chem. Lett.  2003,  13:  4047 
    Search in Google Scholar
  • 8a Matveeva ED. Podrugina TA. Tishkovskaya EV. Tomilova LG. Zefirov NS. Synlett  2003,  2321 
  • 8b Kabachnik MM. Zobnina EV. Beletskaya IP. Synlett  2005,  1393 
  • 8c Bhagat S. Chakraborti AK. J. Org. Chem.  2007,  72:  1263 
    Search in Google Scholar
  • 9a Kabachnik MI. Medved TYa. Dokl. Akad. Nauk SSSR  1952,  689 ; Chem. Abstr. 1953, 47, 2724b
  • 9b Fields EK. J. Am. Chem. Soc.  1952,  74:  1528 
    Search in Google Scholar
  • 10 Boduszek B. Phosphorus, Sulfur Silicon Relat. Elem.  1999,  44:  433 
    Search in Google Scholar
  • 11a Ranu BC. Hajra A. Jana U. Org. Lett.  1999,  1:  1141 
    Search in Google Scholar
  • 11b Chandrasekhar S. Prakash SJ. Jagadeshwar V. Narsihmulu C. Tetrahedron Lett.  2001,  42:  5561 
    Search in Google Scholar
  • 11c Qian C. Huang T. J. Org. Chem.  1998,  63:  4125 
    Search in Google Scholar
  • 12a Kabachnik MM. Zobnina EV. Pavlov VYa. Konstantinov IO. Beletskaya IP. Russ. Chem. Bull.  2005,  54:  262 ; Chem. Abstr., 2006, 144, 432906
    Search in Google Scholar
  • 12b Kabachnik MM. Villemson EV. Beletskaya IP. J. Org. Chem.  2008,  44:  1580 
    Search in Google Scholar
  • 13 Yashin NV. Villemson EV. Chemagin AV. Averina EB. Kabachnik MM. Kuznetsova TS. Synthesis  2008,  464 
    Thieme Connect