Selective functionalization at the small rim of calix[6]arene. Synthesis of novel non-symmetrical N3, N4 and N3ArO biomimetic ligands

Tetrahedron

Volumn 59, Issue 29, 2003, Pages 5563-5568

  Sénèque, Olivier ^a   Reinaud, Olivia ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Biomimetic; Calix 6 arene; Mixed N O ligand; Selective alkylation

Indexed keywords

5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 (AMINO)ETHOXY] 40,42 BIS[(1 METHYL 2 IMIDAZOLYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 (AMINO)ETHOXY] 40,42 BIS[(2 PYRIDINYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 [N [(3,5 DI TERT BUTYL 2 HYDROXY)BENZYL] N PROPYLAMINO]ETHOXY] 40,42 BIS[(1 METHYL 2 IMIDAZOLYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 [[(1 METHYL 2 IMIDAZOLYL)METHYL]AMINO]ETHOXY] 40,42 BIS[(1 METHYL 2 IMIDAZOLYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 [[(3,5 DI TERT BUTYL 2 HYDROXY)BENZYL]AMINO]ETHOXY] 40,42 BIS[(1 METHYL 2 IMIDAZOLYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 [[(3,5 DI TERT BUTYL 2 HYDROXY)BENZYL]AMINO]ETHOXY] 40,42 BIS[(2 PYRIDINYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 [[(5 METHOXY 2 HYDROXY)BENZYL]AMINO]ETHOXY] 40,42 BIS[(1 METHYL 2 IMIDAZOLYL)METHOXY]CALIX[6]ARENE; 5,11,17,23,29,35 HEXA TERT BUTYL 37,39,41 TRIMETHOXY 38 [2 [[(5 NITRO 2 HYDROXY)BENZYL]AMINO]ETHOXY] 40,42 BIS[(1 METHYL 2 IMIDAZOLYL)METHOXY]CALIX[6]ARENE; CALIXARENE; ETHER DERIVATIVE; ETHYLAMINE; HISTIDINE; LIGAND; METAL ION; N TERT BUTYLOXYCARBONYL 2 CHLOROETHYLAMINE; NITROGEN; OXYGEN; SALICYLALDEHYDE; TRIMETHYL ETHER; TYROSINE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BIOMIMETICS; ENZYME ACTIVE SITE; PRIORITY JOURNAL; SYNTHESIS;

ARENE;

EID: 0038721797     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00780-4     Document Type: Article

References (12)

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3. Compared to calix[4]arenes, calix[6]arenes are much more difficult to selectively functionalize at the small rim. This is not only due to their higher number of phenol units but also to their larger size conferring to their cyclic skeleton an increased flexibility.
4. Sénèque O., Rager M.-N., Giorgi M., Reinaud O. J. Am. Chem. Soc. 2000;6183.
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7. This corresponds to the quantity required to deprotonate the two phenol units and to neutralize the 2.5 equiv. of 2-chloromethyl-1-methylimidazole hydrochloride.
8. With NaH, no alkylated product was formed, which may well be due to degradation of 2-chloromethylpyridine.
9. 3ArO ligands could be transformed into ligands with a tertiary amine arm.
10. Ito N.E., Phillips S.E.V., Stevens C., Ogel Z.B., McPherson M.J., Keen J.N., Yadav K.D.S., Knowles P.F. Nature. 350:1991;87.
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