112498-53-0

Upstream product

• 52667-89-7 N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane 
• 4730-54-5 1,4,7-triazacyclononane 
• 67705-38-8 tacnoa 

Downstream Products

• 1309865-22-2 1,4-bis-[1-benzyltetrazol-5-yl]-methyl-1,4,7-triazacyclonane 
• 1309865-25-5 1-formyl-4,7-bis-[1-benzyltetrazol-5-yl]-methyl-1,4,7-triazacyclonane 
• 95388-08-2 N,N'-bis(p-toluenesulfonyl)-1,4,7-triazacyclononane 
• 112498-54-1 4,7-Bis-(toluene-4-sulfonyl)-[1,4,7]triazonane-1-carbaldehyde 

Relevant academic research and scientific papers

Stacked Amido Macrocyclic Complexes: Synthesis and Single Crystal X-Ray Structure of Na(BF4)2(NO3)

The synthesis of bi-functional derivatives of aneN3 is described; the structure of Na(BF4)2(NO3) shows a central - core with the O-donor of the amide moiety of successive 2+ cations bound to Na+ to give a stacked str

Complexation of zinc(II) and cadmium(II) by hydroxyethyl- and bis(hydroxyethyl)-1,4,7-triazacyclononane in water

The complexation of Zn2+ by hydroxyethyl- and bis(hydroxyethyl)-1,4,7-triazacyclononane ((2) and (3)) in aqueous solution at 298.2 K and I = 0.10 mol dm-3 (NaNO3) is characterized by log(K/dm3 mol-1) = 10.45 ± 0.05 and 11.32 ± 0.02 and a deprotonation assigned to coordinated water is characterized by pKa = 8.87 ± 0.11 and 8.50 ± 0.03, respectively. For the analogous Cd2+ complexes log(K/dm3 mol-1) = 8.74 ± 0.02 and 9.79 ± 0.02, respectively, and no deprotonation of coordinated water is detected. The synthesis of (2) is described.

An electroneutral macrocyclic iron(II) complex that enhances MRI contrast in vivo

The first example of a macrocyclic ferrous complex, where two tetrazolyl pendent arms compensate the charge of the metal center, is synthesized and examined for its capacity to enhance MRI contrast in vitro and in vivo in the mouse.

Synthesis and characterisation of pendant-arm amino derivatives of 1,4,7-triazacyclononane and alkyl-bridged bis(1,4,7-triazacyclononane) macrocycles and complexation to Cu(II)

The new pentadentate and bis(pentadentate) ligands 1-methyl-4,7-bis(3-aminopropyl)-1,4,7-triazacyclononane 6 and 1,2-bis[4,7-bis(3-aminopropyl)-1,4,7-triazacyclonon-1-yl]ethane 14 have been synthesised by reaction of acrylonitrile with the corresponding macrocyclic precursors and subsequent reduction of the nitrile groups with BH3*THF. Cu(II) complexes of the two ligands having formulations [Cu(6)][BF4]2 and [Cu2(14)][PF6]4*6MeCN, respectively, have been prepared and structurally characterised. Both complexes exhibit distorted square-based pyramidal geometries about the metal centres with the two primary amino groups belonging to the pendant arms occupying basal positions [Cu-Nap 2.257(6), Cu-Neq 2.026(6)-2.074(5) Angstroem for [Cu(6)]2+, and 2.337(2) and 2.038(3)-2.085(3) Angstroem for [Cu2(14)]4+]. The binuclear complex [Cu2(14)]4+ is centrosymmetric about the ethane bridge with the two pentadentate compartments oriented away from one another to give a transoid anti-configuration with a MeCN molecule interacting with each Cu(II) centre at 2.710(4) Angstroem. Both complexes have also been characterised by electronic and EPR spectroscopy and by cyclic voltammetry, and their properties compared to those of Cu(II) complexes of analogous macrocyclic ligands having 2-methylpyridyl pendant arms.

Synthesis, structure and characterisation of amido derivatives of aneN3 (1,4,7-triazacyclononane)

The amido species OHCaneN3 (1-formyl-1,4,7-triazacyclononane), aneN3H>BPh4, (OHC)3aneN3 (1,4,7-triformyl-1,4,7-triazacyclononane) and (PhOC)3aneN3 (1,4,7-tribenzoyl-1,4,7-triazacyclononane) have been synthesised, characterised and their cr

Selective derivatisation of aza macrocycles

A range of selectively functionalised compounds derived from 1,4,7-triazacyclononane ([9]aneN3), including 4,7-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane-1-carbaldehyde (H2L1), 1-benzyl-4,7-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane (H2L2) and 1,4-bis(2-hydroxy-2-methylpropyl)-1,4,7-triazacyclononane (H2L3), has been prepared. The structure of H2L3·CHCl3 shows a disordered macrocyclic ring with the major conformer refining to a site occupancy of 0.663(8), and both disordered rings adopting a [333] conformation. The pendant alcohol arms were not disordered and were found to be hydrogen bonded to a CHCl3 solvate molecule with H ... O(1) and H ... O(4) distances of 1.73 and 1.81 A respectively. The structure of Na[Cu(H2L1)(NCMe)][BF4]2[NO 3] shows the copper(II) centre in the [Cu(H2L1)(NCMe)]2+ cation bound to two amine donors and two alcohol donors of H2L1 and to a MeCN molecule. The Cu-N bond lengths lie in the range 1.984(3)-2.015(3) A. Both alcohol donors are protonated, with one short Cu-O(16) bond of 1.963(3) A and one long Cu-O(21) bond of 2.252(3) A. There is also a sixth longer-range interaction of the copper(II) centre with the amide N [N(1)] of H2L1 at a distance of 2.611(5) A, confirmed by the loss of planarity of the C(2)-C(9)-N(1)-C(10)-O(11)-H(10) amide fragment to give a dihedral angle between the planes defined by C(2)-C(9)-N(1) and N(1)-C(10)-O(11)-H(10) of 27.1(4)°. The structure is completed by interaction of O(11) with a Na+ ion which itself bridges to BF4- counter anions leading to a central infinite core of [Na(BF4)2]- aggregates onto which are attached the [Cu(H2L1)(NCMe)]2+ cations. The complex [Cu(H2L2)(OH2)][NO3]2 shows the six-co-ordinate copper(II) centre bound to the three amine and two alcohol donors of H2L2 and to one water molecule. There are four short bonds [to N(7), N(4), O(40) and O(1)] in the range 1.961(5)-2.073(6) A and two longer bonds to N(1) and O(70) at 2.308(5) and 2.313(5) A respectively. The H atoms of the water molecule [O(1)] and one of the pendant arms [O(40)] also make hydrogen-bonding contacts with the nitrate counter ions.

Selective N-Protection of Medium-ring Triamines

Efficient schemes for selective N-protection of 1,4,7-triazacyclononane and 1,5,9-triazacyclododecane and for synthesis of related bis-coronands are based upon the synthetic intermediacy of tricyclic orthoamides.