Synthesis and characterization of hexasubstituted azacryptands

Tetrahedron Letters

Volumn 51, Issue 50, 2010, Pages 6521-6525

  De Rycke, Nicolas ^a   Marrot, Jérôme ^a   Couty, François ^a   David, Olivier R P ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Azacryptand; Imine condensation; Macrocyclic chemistry; Nitrogen basicity; Nitrogen ligand

Indexed keywords

ALDEHYDE; AMINE; AROMATIC COMPOUND; HETEROCYCLIC COMPOUND; IMINE;

ALKYLATION; ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROPHOBICITY; MOLECULAR STABILITY; POLYMERIZATION; PROTON TRANSPORT; SYNTHESIS; THERMODYNAMICS; TITRIMETRY;

EID: 78650244765     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.019     Document Type: Article

References (19)

1. (a) Zhong, Z.; Postnikova, B. J.; Hanes, R. E.; Lynch, V. M.; Anslyn, E. V. Chem. Eur. J. 2005, 11, 2385-2394;
2. (b) Ilioudis, C. A.; Tocher, D. A.; Steed, J. W.J. Am. Chem. Soc. 2004, 126, 12395-12402;
3. (c) Hennrich, C.; Anslyn, E. V. Chem. Eur. J. 2002, 8, 2218-2224;
4. d)Niikura, K.; Bisson, A P.; Anslyn, E. V.J. Chem. Soc., Perkin Trans. 2 1999, 1111-1114;
5. (e) Bisson, A. P.; Lynch, V. M.; Monahan, M.-K. C.; Anslyn, E. V. Angew. Chem., Int. Ed. 1997, 36, 2340-2342.
6. Davis, A. P. Org. Biomol Chem. 2009, 7, 3629-3638.
7. For a seminal use of hexaimine condensation in a cryptand synthesis see (a) MacDowell, D.; Nelson, J. Tetrahedron Lett. 1988, 29, 385-386;
8. (b) Francesconi, O.; Lenco, A.; Monetl, G.; Nativi, C.; Roelens, S. Angew. Chem., Int. Ed. 2006, 45, 6693;
9. (c) Arunachalam, M.; Ravikumar, I.; Ghosh, P.; Org. Chem. 2008, 73, 9144-9147. and references cited therein;
10. (d) Mateus, P.; Delgado, R.; Brandão, P.; Carvalho, S.; Félix, V. Org. Biomol. Chem. 2009, 7, 4661-4673;
11. (e) Mateus, P.; Delgado, R.; Brando, P.; Félix, V. J. Org. Chem. 2009, 74, 8638-8646.
12. This compound is prepared in two steps starting from dihydroxynaphthalene and involves a double bromination followed by lithiation and formylation with DMF; see Supplementary data.
13. Gu, J.; Yulan, W.; Chen, W.-Q.; Dong, X.-Z.; Duan, X.-M.; Kawata, S. New J. Chem. 2007, 31, 63-68.
14. This compound is prepared in three steps from chelidamic acid; this synthesis will be reported elsewhere.
15. Bottino, F.; Di Grazia, M.; Finocchiaro, P.; Fronczek, F. R.; Mamo, A.; Pappalardo, S. J. Org. Chem. 1988, 53, 3521-3529.
16. Saeed, M. A.; Fronczek, F. R.; Hossain, Md. A. Chem. Commun. 2009, 64096411.
17. Bernhardt, P. V.; Harrowfield, J. M.; Hockless, D. C. R.; Sargeson, A. M. Inorg. Chem. 1994, 33, 5659-5670;
18. Ling, R.; Yoshida, M.; Mariano, P. S. J. Org. Chem. 1996, 61, 4439-4449.
19. a for AcOH and TFA in DMSO are 12.3 and 3.45, see: Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.