Synthesis of 2-azacycl[3.2.2]azine

Fuentes, Omar; Paudler, William W.

doi:10.1021/jo00897a006

Cited by 41 publications

(33 citation statements)

References 2 publications

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“…6-Methyl-2-methylaminopyridine was prepared according to a previously reported procedure. [59] Figure 7. Relaxation kinetics of the photoinduced fraction of the ethanol solvates of 1 (stars), 2 (empty circles), and 3 (full circles) at 9 K. The converted fraction is normalized at 1 when t = 0.…”

Section: Methodsmentioning

confidence: 99%

Tuning the Charge Distribution and Photoswitchable Properties of Cobalt–Dioxolene Complexes by Using Molecular Techniques

Beni

Dei

Laschi

et al. 2008

Chemistry A European J

123

220

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A series of cobalt complexes [Co(Me(n)tpa)(diox)]PF(6)sol (diox=3,5-di-tert-butyl-1,2-dioxolene; sol=ethanol, toluene; tpa=tris(2-pyridylmethyl)amine) were prepared by using tripod-like Me(n)tpa (n=0, 1, 2, 3), derived from tpa by successive introduction of methyl groups into the 6-position of the pyridine moieties, as an ancillary ligand. The steric hindrance induced by this substitution modulates the redox properties of the metal acceptor, thus determining the charge distribution of the metal-dioxolene moiety at room temperature. All of these complexes were characterised by using diffractometric studies, electronic spectroscopic analysis, and magnetic susceptibility measurements. In the solid state, the [Co(Me(n)tpa)(diox)](+) ions (n=0, 1) can be described as diamagnetic cobalt(III)-catecholato derivatives, whereas a cobalt(II)-semiquinonato description seems appropriate for the paramagnetic [Co(Me(3)tpa)(diox)](+) complex. The complex [Co(Me(2)tpa)(diox)]PF(6)C(2)H(5)OH undergoes entropy-driven valence tautomeric interconversion at room temperature. Optically induced valence tautomerism was observed by irradiation of [Co(Me(n)tpa)(diox)]PF(6) complexes (n=0, 1, 2) at cryogenic temperatures. The different relaxation kinetics of the photoinduced metastable phases are related to the respective free-energy changes of the interconversion, as estimated by cyclic voltammetric experiments at room temperature, and to the different lattice interactions, as supported by structural data. These results show the importance of molecular techniques for controlling the relaxation properties of photoinduced metastable species. At the same time, this behaviour strongly suggests that this paradigm exhibits intrinsic limits because of the less controllable factors that affect the process.

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Section: Methodsmentioning

confidence: 99%

Tuning the Charge Distribution and Photoswitchable Properties of Cobalt–Dioxolene Complexes by Using Molecular Techniques

Beni

Dei

Laschi

et al. 2008

Chemistry A European J

123

220

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“…calc. for C31 H 35 N 5 O 5 : C 66.77, H 6.33, N 12.56; found: C 66.59, H 6.34, N 12.37. FAB-MS (Nibeol; pos.…”

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confidence: 97%

Tuning the Properties of Copper(II) Complexes with Tetra‐ and Pentadentate Bispidine (=3,7‐Diazabicyclo[3.3.1]nonane) Ligands

Comba

Laorden

Pritzkow

2005

Helvetica Chimica Acta

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Dedicated to Professor AndreÂ E. Merbach on the occasion of his 65th birthdayThe synthesis of a series of tetra-and pentadentate bispidine-type ligands (bispidine 3,7-diazabicyclo[3.3.1]nonane) ± tetradentate ligands are donor-substituted at C(2) and C(4), pentadentate ligands have an additional donor at N(3) or N(7), with pyridine, 2-methylpyridine, or quinoline donor moieties ± and of their Cu II complexes are reported, together with single-crystal structural analyses and solution studies (electrochemistry, electronic and EPR spectroscopy). Depending on the ligand geometry and on the co-ligands (solvent or counter anion), there are various structural forms (pseudo-Jahn ± Teller elongation along all three molecular axes), and the structural data are correlated with the spectroscopic and electrochemical parameters.Introduction. ± The transition-metal-ion coordination chemistry of bispidine-type ligands (bispidine 3,7-diazabicyclo[3.3.1]nonane; see L1 ± L12 for ligand structures discussed in this publication) has attracted some attention due to the salient structural properties [1 ± 3], high complex stabilities and uncommon metal-ion selectivities [4] and, in particular, because of their interesting reactivities [5 ± 9], specifically with respect to efficient [10] and tuneable [7] [8] substrate binding and activation. An important feature is that bispidine molecules are generally easy to prepare, and they are obtained in high yield [11 ± 14], and that mono-as well as dinucleating ligands with various donor sets in well-defined and rigid geometries may be prepared (bi-, tetra-, penta-, and hexadentate ligands, preorganized for planar, square-pyramidal and cisoctahedral coordination geometries) [15 ± 20].Due to the rigidity of the adamantane-derived bispidine backbone and the elasticity of the coordination geometry, interesting types of structural variations have been observed [1 ± 3] [21] [22]. In particular, for penta-and hexacoordinate Cu II complexes, it was possible to isolate and structurally characterize ± in dependence of i) the orthosubstituent of the pyridine donors at C(2) and C(4) (H or Me) [7], ii) the substituent at N(7) [3] [21], or iii) the co-ligands [22] ± complexes with the tetragonal elongation (pseudo-Jahn ± Teller axis) along any of the three molecular axes.So far, the chance to vary the donor set by a variation of the aldehyde and amine components in the two Mannich condensation steps (see Scheme) has not been used extensively. We, therefore, report here the syntheses of six new tetra-and pentadentate bispidine ligands with 2-methylpyridine and quinoline donors, and the structural, electrochemical, and spectroscopic properties of their Cu II complexes. The structural properties, specifically with respect to the mode of pseudo-Jahn ± Teller-type distortion,

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“…The mixture was chromatographed on silica gel with aqueous acetone as the eluent, and then the eluate was purified by chromatography on MCI gel CHP-20P. The desired cephalosporins (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(21)(22)(23)(24)(25) were isolated as amorphous powders in yields of 2-13%. bacteria were determined by the standard serial 2-fold agar dilution method.…”

Section: Chemistrymentioning

confidence: 99%

“…The MICof 7 against S. aureus and Enterà"obacter cloacae was higher than that of 1. Table 3 shows the MICs of a variety of substituted imidazo[l, [2][3][4][5][6]pyridazinium cephalosporins (ll~16). Amongthe cephalosporins tested, the 6-thiomethyl derivative (16) showed more potent activity against S. aureus and E. cloacae than 2, whereas the activity of the others against those was similar or inferior to that of 2.…”

Section: Chemistrymentioning

confidence: 99%

Studies on condensed-heterocyclic azolium cephalosporins. II. Synthesis and antibacterial activity of 7.BETA.-(2-(2-aminothiazol-4-yl)-2(Z)-alkoxyiminoacetamido)-3-(condensed-heterocyclic azolium)methyl-3-cephem-4-carboxylates.

et al. 1991

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Synthesis of 2-azacycl[3.2.2]azine

Cited by 41 publications

References 2 publications

Tuning the Charge Distribution and Photoswitchable Properties of Cobalt–Dioxolene Complexes by Using Molecular Techniques

Tuning the Charge Distribution and Photoswitchable Properties of Cobalt–Dioxolene Complexes by Using Molecular Techniques

Tuning the Properties of Copper(II) Complexes with Tetra‐ and Pentadentate Bispidine (=3,7‐Diazabicyclo[3.3.1]nonane) Ligands

Studies on condensed-heterocyclic azolium cephalosporins. II. Synthesis and antibacterial activity of 7.BETA.-(2-(2-aminothiazol-4-yl)-2(Z)-alkoxyiminoacetamido)-3-(condensed-heterocyclic azolium)methyl-3-cephem-4-carboxylates.

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