Synthesis 2006(18): 3134-3140  
DOI: 10.1055/s-2006-942502
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Efficient Syntheses of Polyamines Bearing 1H-Tetrazol-5-yl Units on Their Amino Functions

Constantinos M. Athanassopoulos*, Thomas Garnelis, George Magoulas, Dionissios Papaioannou
University of Patras, Department of Chemistry, University Campus, 26500 Rion, Patras, Greece
Fax: +30(261)0997156; e-Mail: kath@chemistry.upatras.gr;
Further Information

Publication History

Received 31 March 2006
Publication Date:
19 July 2006 (online)

Abstract

Linear N-benzyl-N′-trityl-α,ω-diamines and N α, N ω-ditritylpolyamines were efficiently converted into the corresponding N-(1-benzyltetrazol-5-yl)-substituted derivatives upon treatment with benzyl isothiocyanate followed by reaction of the thus-obtained thioureas with azidotrimethylsilane under Mitsunobu reaction conditions.

    References

  • 1a Ford RE. Knowles P. Lunt E. Marshal SM. Penrose AJ. Ramsden CA. Summers AJH. Walker JL. Wright DE. J. Med. Chem.  1986,  29:  538 
  • 1b Peet NP. Baugh LE. Sunder S. Lewis JE. Matthews EH. Olbering EL. Shah DN. J. Med. Chem.  1986,  29:  2403 
  • 2 White AD. Greswell MW. Chucholowski AW. Blankley CJ. Wilson MW. Bousley RF. Essenburg AD. Hamelehle KL. Krause BR. Stanfield RL. Dominick MA. Neub M. J. Med. Chem.  1996,  39:  4382 
  • 3 Castro JL. Ball RG. Broughton HB. Russell MN. Rathbone D. Watt AP. Baker R. Chapman KL. Fletcher AE. Patel S. Smith AJ. Marshall GR. Ryecroft W. Matassa VG. J. Med. Chem.  1996,  39:  842 
  • 4 Hallinan EA. Tsymbalov S. Dorn CR. Pitzele BS. Hansen DW. Moore WM. Jerome GM. Connor JR. Branson LF. Widomski DL. Zhang Y. Currie MG. Manning PT. J. Med. Chem.  2002,  45:  1686 
  • 5a Batey RA. Powell DA. Org. Lett.  2000,  2:  3237 
  • 5b Yu Y. Ostresh JM. Houghten RA. Tetrahedron Lett.  2004,  45:  7787 
  • 6 Athanassopoulos CM. Garnelis T. Vahliotis D. Papaioannou D. Org. Lett.  2005,  7:  561 
  • 7 Mamos P. Karigiannis G. Athanassopoulos C. Bichta S. Kalpaxis D. Papaioannou D. Sindona G. Tetrahedron Lett.  1995,  36:  5187 
  • 8 Martin-Martinez M. Herranz R. Garcia-Lopez MT. Gonzalez-Muniz R. Tetrahedron  1996,  52:  13991 
  • 9 Vassis S. Govaris I. Voyagi K. Mamos P. Papaioannou D. Tetrahedron Lett.  2002,  43:  2597 
  • 10 Tsiakopoulos N. Damianakos C. Karigiannis G. Vahliotis D. Papaioannou D. Sindona G. Arkivoc  2002,  (xiii):  79 ; http://www.arkat-usa.org
  • 11 Athanassopoulos CM. Garnelis T. Pantazaka E. Papaioannou D. Tetrahedron Lett.  2004,  45:  8815