Neutral water-soluble indium complexes of 3-hydroxy-4-pyrones and 3-hydroxy-4-pyridinones

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. Can. J. Chem. 69, 893 (1991). The aluminum, gallium, and indium tris(1igand) complexes of 3-hydroxy-2-methyl-1-n-propyl-4-pyridinone and l-tz-butyl-3-hydroxy-2-methyl-4-pyridinone have been prepared and characterized. All six compounds were prepared in a one-pot synthesis from maltol, n-propyl-, or n-butylamine and an appropriate metal(II1) salt, and were completely characterized (IR, FAB-MS, 'H NMR, ' '~1 NMR, elemental analysis). Three of the six complexes were studied by single-crystal X-ray diffraction and were found to form trihydrates, unlike their 1-methyl and 1-ethyl analogues, which formed dodecahydrates. The n-butylpyridinone complex A1(CIOH14N02)3.3H20 (Al(nbp)3.3H2O) and 11-propylpyridinone complexes A1(C9H12N02)3.3H20 (A l ( n~p )~. 3 H~O ) , and Ga(C9H12N02)3.3H20 ( G a ( n p~)~. 3 H~O ) were essentially isostructural, crystallizing in the space group On a prCparC et caractiris6 les complexes tricoordinks de l'aluminium, du galliumet de l'indium avec la 3-hydroxy-2-mkthyll-n-propyl~pyridin-4-one et la 1-11-butyl-3-hydroxy-2-mithyl-pyridin-4-On a prepare les six composCs par des synthkses "bouillabaisses" impliquant le maltol, les tz-propyl-ou n-butyl-amines et le sel mCtallique(II1) appropriC et on les a caractCrisks compl&tement par ir, sm-bar, rmn du 'H, rmn du "Al et analyse ClCmentaire. On a examine trois des six complexes par diffraction des rayons-X par des cristaux uniques et on a trouvC qu'ils forment des trihydrates alors que leurs analogues I-mkthyle et 1-Cthyle foment des dodCcahydrates. Le complexe de la n-butylpyridinone, A1(CloH14N02)3.3H20 ( A l ( n b~)~. 3 H~O ) et les complexes de la n-propylpyridinone, A1(C9H12N02)3.

Section: Introductionmentioning

confidence: 99%

“…lo), formed tris(ligand)metal(III) dodecahydrate complexes when the N-substituent was methyl or ethyl (the complexes M ( d~p )~ and M ( m e~p )~) (4)(5)(6)(7)(8). These crystallized in a manner unknown amongst inorganic hydrates; unusual hydrogen bonding was observed in the solid state.…”

Section: Introductionmentioning

confidence: 99%

1-n-Propyl- and 1-n-butyl-3-hydroxy-2-methyl-4-pyridinone complexes of group 13 (IIIA) metal ions

Simpson¹,

Rettig²,

Trotter³

et al. 1991

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“…These complexes are tris(bidentate ligand)metal(III) species, and incorporate as ligands various pyrones (e.g. maltol, 1) (4, 5 ) , N-substituted-3-hydroxy-4-pyridinones (2) (6)(7)(8) and isomaltol (3) (9). The properties of interest are hydrolytic stability, water solubility, neutral charge, and lipophilicity, all occurring simultaneously.…”

Section: Introductionmentioning

confidence: 99%

“…(or 13) ions (8) and certain of the complexes formed unusual solid state hydrogen bonding arrays (6,7). In efforts to extend the coexistence of these four properties into hexadentate analogs of these binding moieties, we have undertaken model studies involving the preparation of some new ligands for the group 13 ions.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 2- and 4-substituted 3-hydroxy-5-methylfurans and the aluminum and gallium complexes of 3-hydroxy-5-methyl-2-(N-methylformamido)furan

Lutz¹,

Clevette²,

Hoveyda³

et al. 1994

Can. J. Chem. 72, 1362 (1994.In model studies designed to study the synthesis of potentially hexadentate chelates based on the linkage of three furan rings to a triamine via amide linkages, new 2-and 4-substituted 3-hydroxy-5-methylfurans have been prepared. Particularly, 3-hydroxy-5-methyl-(N-methylforrnamido)furan (Hahm) and its Al and Ga complexes (M(ahm)3) have been prepared and thoroughly characterized by a variety of techniques, in the solid state and in solution. Solution equilibrium studies ( p = 0.6 M NaCl, 25°C) uncovered a complicated set of equilibria in the ~l~+ / H a h m system; the solution potentiometric data were best explained by the presence of mixed ligand (

“…1. Neither the metal-pyrone complexes nor the product ligands were isolated because the aim of this work is the direct preparation; however, the conditions are completely compatible with those used in their formation (3,4). The accepted mechanism for the preparation of a 4-pyridinone by conversion of an appropriate 4-pyrone is nucleophilic attack by a primary amine, followed by ring opening, 1 elimination of water, and ring closure to give the 4-pyridinone 1 (23).…”

mentioning

confidence: 99%

One-pot synthesis of N-substituted-3-hydroxy-4-pyridinone chelate complexes of aluminum, gallium, and indium

Zhang¹,

Hui²,

Orvig³

1989

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Thispaper is dedicated to Professor Ronald J . Gillespie on the occasiorz of his 65th birthday ZAIHUI ZHANG, T. L. THOMAS HUI, and CHRIS ORVIG. Can. J. Chem. 67, 1708Chem. 67, (1989. A series of tris(3-hydroxy-2-methyl-4-pyridinonato)metal(III) and tris(3-hydroxy-6-hydroxymethyl-4-pyridinonat0)-metal(II1) complexes have been prepared in water by one-pot synthesis directly from maltol and kojic acid, respectively, and the metal ion (M = AI, Ga, In) with an appropriate amine. The pyridinones have substituents at the ring nitrogen atom (CH3, C2H5). The tris(3-hydroxy-4-pyronato)metal(III) complexes are formed in situ and these undergo nucleophilic attack by the primary amine; the appropriate tris(3-hydroxy-4-pyridinonato)metal(III) complexes are obtained. This method bypasses the sequential syntheses of ligand and metal complex, and has improved the yields of the tris(1igand)metal complexes, in particular by making them much more easily accessible. The electronic effects of binding the pyrone to the metal ions and of the substituents on the pyrone ring on the reactivity are discussed.Key words: 3-hydroxy-4 pyridinone complexes, group 13 metal ions, one-pot synthesis.ZAIHUI ZHANG, T. L. THOMAS HUI et CHRIS ORVIG. Can. J. Chem. 67, 1708Chem. 67, (1989. Utilisant des reactions de type <