2-Methyl-3-hydroxy-4-pyridinones

Despite their importance in many pharmacological uses and potential applications, solubilities of hydroxypyranones, hydroxypyridinones, and their complexes have not been extensively and systematically investigated and established. This situation contrasts sharply with that for partition coefficients, as will become apparent in the following section. The solubility of maltol in water is approximately 0.1moldm , of ethyl maltol 0.13 mol dm, at 298 K. 1,2-Alkyl-3-hydroxy-4-pyridinones show the expected decrease in water-solubility as the sizes of the alkyl groups increase solubilities - in water at 298 K - of l-aryl-2-methyl-3-hydroxy-4-pyridinones decrease from 9 X 10 mol dm for the 1-phenyl compound through 6 x lO- moldm for l-(4 -tolyl) to 6 x 10 mol dm for l-(4 -re-hexyl-phenyl) (37). 

Somewhat surprisingly, maltol (2-methyl-3-hydroxy-4-pyrone), an aromatic analogue to a-hydroxy carboxylic acids, shows little inclination toward formation of dimeric complexes. Rather, the chemistry is more in parallel with that of oxalate, and an x-ray structure of the bismaltolato complex [25] shows a cis octahedral coordination similar to that found for the oxalate complex. Under mildly acidic to moderately basic solution, the major complexes are mono- and bisligand derivatives. The corresponding vanadium chemical shifts are -509 and -496 ppm, respectively [25,26], The closely related amines, 2-methyl-3-hydroxy-4-pyridinone and its N-... 

CYCLOPENTADlENE AND DICYCLOPENTADlENE] (Vol 7) l-Hydroxy-4-methyl-6-(2,4,4-tri-methylpentyl)- 2-(lIT) pyridinone,ethanolamine salt [68890-66-4]... 

Table 11 summarizes the main results on the tautomerism of mono-hydroxy-, -mercapto-, -amino- and -methyl-azines and their benzo derivatives, in water. At first sight the equilibrium between 2-hydroxypyridine (71) and pyridin-2-one (72) is one between a benzenoid and a non-benzenoid molecule respectively (71a 72a). However, the pyridinone evidently... 

Pyridin-4-one, 1 -hydroxy-2,6-dimethyl-hydrogen-deuterium exchange reactions, 2, 196 Pyridin-4-one, 1-methyl-hydrogen-deuterium exchange, 2, 287 pK 2, 150 Pyridin-2-one imine tautomerism, 2, 158 Pyridin-2-one imine, 1-methyl-quaternization, 4, 503 Pyridin-4-one imine tautomerism, 2, 158 Pyridinone methides, 2, 331 tautomerism, 2, 158 Pyridinones acylation, 2, 352 alkylation, 2, 349 aromaticity, 2, 148 association... 

RN 29342-05-0 MF C HnNO MW 207.27 EINECS 249-577-2 CN 6-cyclohexyl-l-hydroxy-4-methyl-2(l/f)-pyridinone... 

APM-3,4-HOPY is a bidentate 3-hydroxy,4-pyridinone featuring a propylamine moiety attached to the pyridine N and a methyl group on carbon 2 of the pyridine ring. sThis value is reported as a lh n-... 

Trenhopo is a hexadentate tripodal ligand N(CH2CH2NHCOX)3 with X being 6-methyl-3-hydroxy-2-pyridinonate. 

Figure 1 Transfer chemical potentials for selected iron complexes from water into aqueous methanol (on the molar scale, at 298 K). Ligand abbreviations not appearing in the list at the end of this chapter are acac = acetylacetonate (2,4-pentanedionate) dmpp = l,2-dimethyl-3-hydroxy-4-pyridinonate, the anion from (24) malt = maltolate (2-methyl-3-hydroxy-4-pyranonate, the anion from (233)).

Job plots have established the stoichiometry of several iron(III)-3-hydroxy-2-methyl-4(l//)-pyridinone systems in aqueous solution.Stability constants have been determined for 1,2-dimethyl-, 1,2-diethyl-, and several other 3-hydroxy-4-pyridinonato-iron(III) complexes. " These data supplement and update the long-standing set of log / 3 values for... 

Table 11 summarizes the main results on the tautomerism of mono-hydroxy-, -mercapto-, -amino- and -methyl-azines and their benzo derivatives, in water. At first sight the equilibrium between 2-hydroxypyridine (71) and pyridin-2-one (72) is one between a benzenoid and a non-benzenoid molecule respectively (71a 72a). However, the pyridinone evidently has a continuous cyclic p- orbital system, containing six it- electrons, the usual aromatic count, if the carbonyl group contributes none. This assumption implies the formula (72b), from which by redistribution of electrons we arrive at (72c), which has the same benzenoid system as (71a). Further canonical forms (71b, 71c) can be drawn of (71) which correspond to the non-benzenoid forms of (72). The elusive property of aromaticity is therefore possessed by both tautomers, although not necessarily by both equally. When the carbonyl oxygen of (72) is replaced by less electronegative atoms, as in the imine tautomers of amino heterocycles, or the methylene tautomers of methyl derivatives, the tendency towards polarization in forms corresponding to (72b) and (72c) is considerably less, and the amino and methyl tautomers are therefore favoured in most instances. 

Numerous examples of complexation of group III and IV metals with simple chelate ligands were reported between 1995 and 2006. Those include, but are not limited to, the formation of Sn(etma)2Cl2 (etma = ethylmaltol), Sn(mcpp)(ll3( I IT)) (mepp = 1 -methyl-2-ethyl-3-hydroxy 4-pyridinone) <2000POL399>, 24 tin(iv) 2,2-di- -butyl- and... 

V Chemical Shifts and Formation Constants for Selected 2-Methyl-3-Hydroxy 4-Pyrone and 4-Pyridinone Complexes of Vanadate at pH 7.0... 

Chemical Name 2(lH)-Pyridinone, 6-cyclohexyl-l-hydroxy-4-methyl-Common Name Cicloprox Structural Formula ... 

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