6533b837fe1ef96bd12a26a6

RESEARCH PRODUCT

Polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes

Santiago V. LuisBeatriu EscuderEnrique García-españaJuan F. MiravetM. Isabel Burguete

subject

Sulfonylchemistry.chemical_classificationchemistry.chemical_compoundTosylchemistryStereochemistryOrganic ChemistryDrug DiscoveryAmine gas treatingProtecting groupBiochemistryMedicinal chemistry

description

Abstract A series of polyaza[n](1,4)naphthalenophanes and polyaza[n](9,10)anthracenophanes have been prepared by using the Fukuyama's protecting group (2- or 4-nitrophenyl sulfonyl) in a one-pot cyclization–deprotection reaction. Global yields for the purified products are comparable with those obtained for other polyazacyclophanes using the tosyl group as the amine protecting group. Their structural study has been carried-out by NMR showing a high rigidity for the smaller cycles and a more dynamic behaviour for the largest member of the series. The free energy barrier for the rotational equilibrium for compound 25 is about 3 kcal/mol lower than that calculated for analogous N-tosylated macrocycles.

yearjournalcountryeditionlanguage
2002-04-01Tetrahedron
https://doi.org/10.1016/s0040-4020(02)00180-1