Synthesis of a new ditopic ligand possessing linear and cyclic tetraaza subunits

Synthetic Communications

Volumn 38, Issue 10, 2008, Pages 1589-1600

  Prokhorov, Anton ^a   Bernard, Hélène ^a   Bris, Nathalie Le ^a   Marquet, Nicolas ^a   Handel, Henri ^a  

^a UNIVERSITÉ DE BRETAGNE OCCIDENTALE   (France)

Author keywords

Bisaminal; Cyclam; Ditopic ligand; Linear tetraamine; Phosphoryl group

Indexed keywords

3 BROMOPROPYL; CYCLIC TETRAAZA; HETEROCYCLIC COMPOUND; LIGAND; PROPANE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS; X RAY ANALYSIS;

EID: 42549155200     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910801929481     Document Type: Article

References (15)

1. (a) Kuksa, V.; Buchan, R.; Lin, P. K. T. Synthesis of polyamines, their derivatives, analogues and conjugates. Synthesis 2000, 9, 1189-1207;
2. (b) Karigiannis, G.; Papaioannou, D. Structure biological activity and synthesis of polyamines analogues and conjugates. Eur. J. Org. Chem. 2000, 1841-1863;
3. (c) Liang, F.; Wan, S.; Li, Z.; Xiong, X.; Yang, L.; Zhou, X.; Wu, C. Medical applications of macrocyclic polyamines. Curr. Med. Chem. 2006, 13, 711-727.
4. (a) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S. Thermodynamic and kinetic data for macrocycle interaction with cations, anions, and neutral molecules. Chem. Rev. 1995, 95, 2529-2586;
5. (b) Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications. Chem. Rev. 1999, 99, 2293-2352;
6. (c) Kaden, T. A. Dinuclear metal complexes of bis-macrocyles. Coord. Chem. Rev. 1999, 190-191, 371-389.
7. (a) Bianchi, A.; Bowman-James, C.; Garcia-España, E. Supramolecular Chemistry of Anions; Wiley-VCH: New York, 1997;
8. (b) García-España, E.; Díaz, P.; Llinares, J. M.; Bianchi, A. Anion coordination chemistry in aqueous solution of polyammonium receptors. Coord. Chem. Rev. 2006, 250, 2952-2986.
9. Soibinet, M.; Gusmeroli, D.; Siegfried, L.; Kaden, T. A.; Palivan, C.; Schweiger, A. Kinetics and mechanism of the stepwise complex formation of Cu(II) with tren-centered tris-macrocycles. Dalton Trans. 2005, 2138-2146.
10. Kaden, T. A. Metal complexes of ditopic and polytopic macrocyclic ligands. J. Incl. Phenom. Macrocycl. Chem. 2004, 49, 3-9.
11. Filali, A.; Yaouanc, J. J.; Handel, H. Stoichiometric mono-N-functionalization of tetraazamacrocycles via phosphoryl-protected intermediates. Angew. Chem., Int. Ed. Engl. 1991, 30, 560-561.
12. Claudon, G.; Le Bris, N.; Bernard, H.; Handel, H. Powerful N-monoalkylation of linear tetraamines via bisaminal intermediates. Eur. J. Org. Chem. 2004, 5027-5030.
13. (a) Bernard, H.; Del Rio Garcia, E.; Ferec, S.; Kervarec, N.; Handel, H. The unexpected conversion of 1,5,8,12-tetraazadodecane-glyoxal bisaminal into its amidinium salt in an acidic medium. Eur. J. Org. Chem. 2003, 255-258;
14. (b) Tripier, R.; Chuburu, F.; Le Baccon, M.; Handel, H. Phenylglyoxal for polyamines modification and cyclam synthesis. Tetrahedron 2003, 59, 4573-4579.
15. Oget, N.; Chuburu, F.; Handel, H.; Toupet, L. Cyclen phosphine oxide: hydrogen bonding and transannular N! P interaction. J. Chem. Res. 1999, 526-527.