2-Hydroxymethyl-3-methyl-4- pyridine

Complexation via the ligand method of more than 70 % of the Cu and Fe ions in zeolite Y with a mixed tridentate NJ f,O-ligand such as (2-hydroxymethyl) (2-methyl-pyridine)amine (Hbpa) was reported, yielding entrapped Fe(bpa) (8) together with residual uncomplexed rhombohedral Fem with an ESR signal at g = 4.3 and Fe-Fe interactions with g = 2.0/1121 When a more than stoichiometric amount of Hbpa... 

Miscellaneous examples of the photoaddition of solvent and other simple molecules to nitrogen-containing systems have been described. Methoxylation, methylation, and hydroxymethylation arising via ionic and radical pathways have been observed on irradiation of dimethyl pyridine-2,4-dicarboxylate in methanol. The photomethoxylation of methyl pyridine-2-carboxylate in acidified methanol is facilitated by added 4-substituted pyridines such as 4-cyanopyridine an excited complex is thought to be involved. 

The oxidation of the methyl group begins generally with the formation of the hydroxymethyl analog and continues usually until the carboxyl step. This is observed for simple componnds like camphor or 2-methyl-pyridine but also for drugs like tolbutamide and alpidem, explaining the relatively short half-life of these latter compounds. 

Pyridoxine (peer-ih-DOCK-seen) is also known as 3-Hydroxy-4,5-bis(hydroxymethyl)- -methyl pyridine 3-hydroxy-4,5-dime-thylol-2-methylpyridine and vitamin B6. It is a white, odorless, crystalline compound with a slightly bitter taste. The term pyridoxine is also used as a generic term for three compounds with biological activity classified under the term Vitamin Bfc. The three compounds are pyridoxine, pyridoxal, and pyridoxamine. Pyridoxine is usually produced commercially as the hydrochloride, CH3CSHN(0H)(CH20H)2-HC1, which has somewhat different physical characteristics from pyridoxine itself. 

Giorgy and his associates demonstrated that the administration of a factor referred to as vitamin 85 cures a scaly dermatitis of rats produced for the first time by Golderburger and Lily in 1926. The pellagralike dermatitis proved to be resistant to the administration of thiamine, nicotinic acid, and riboflavin. During the first five months of 1938, five different laboratories reported the crystallization and chemical identification of the vitamin. The vitamin was shown to be the 4,5-di-(hydroxymethyl)-3-hydroxy-2-methyl-pyridine. 

A second enzymatic site, which has been selected as a target to direct the chelating potential of the thiosemicarbazone molecule, is pyridoxal phospho-kinase [65], This catalyst is a zinc-requiring enzyme [66] that catalyzes the phosphorylation of pyridoxine at position 5 to form the active coenzyme form. In an effort to accomplish inhibition, 2-formyl-3-hydroxy4,5-bis(hydroxy-methyl)pyridine thiosemicarbazone (117) was synthesized [65]. This was accomplished by two different procedures. The common intermediate, 3-acetoxy-2,4,5-tris(acetoxymethyl)pyridine (111) [67], upon acid hydrolysis afforded 3-hydroxy-2,4,5-tris(hydroxymethyl)pyridine hydrochloride (112), which was treated with hydrogen chloride as a suspension in acetone [68]. The amount of hydrogen chloride taken up by the suspension is a critical factor and. 

The generic term vitamin Be refers to all 3-hydroxy-2-methylpyridine derivatives that exhibit the biological activity of pyridoxine in rats (7). Pyridoxine (3-hydroxy-4,5-bis-(hydroxymethyl)-2-methyl pyridine) should not be used as generic term synonymous with vitamin B. Two other forms of vitamin Be, pyridoxal (PL) and pyridoxamine (PM), differ from pyridoxine (PN) in the respective location of an aldehyde and amine group at the 4 position of the pyridine ring structure (Fig. 1). The 5 -phosphoric ester of pyridoxal, pyridoxal-5 -phosphate (PLP), is the metabolically active form of vitamin Be. Pyridoxamine-5 -phosphate... 

Inactive for rat and Laetobacillua casei 3-Amino-4-ethoxymethyl-5-aminometh-yI-2-methyl-pyridine 3-Amino-4-hydroxymcthyl-5-aminomethyl-2-methyl-pyri-dine 3-Amino-4-bromomethyl-5-aminomethyl-2-methyl-pyridine 3-Hydroxy-4,6-dimethyl-5-aniinomethyl-2-methyl-pyridine Lactone of 3-hydroxy-4-hydroxymeth-yl-5-carboxy-2-methyl-pyridine Lactone of 3-amino-4-hydroxymethyl-5-carboxy-2-methyl-pyridine. 

Minisci reactions have also been applied to these compounds. formation by exposure to w-CPBA and O-methylation with Meerwein s reagent converted 54 into 55. Nucleophilic attack of the hydroxymethyl radical, generated with ammonium sulfate, provides an alternate route to 2-hydroxymethyl pyridines 56. 

Mit neun Hydrid-Aquivalenten Diboran erhalt man als Hauptprodukt 3-Hydroxy-2-methyl-4-hydroxymethyl-pyridin-5-carbonsaure-4 -lacton2 ... 

Hydroxy-2-methyl-4,5-bis-[hydroxymethyl -pyridin-Hydrochlorid (Vitamin B6)8... 

A 6,6-dimethyl-6,7-dihydropyrido[l,2-c]quinazolinium salt was obtained from the reaction of 2-(2-aminophenyl)-pyridine and acetone <1997AJC109>. Reaction of 3-methyl-l,2,3,4-tetrahydroisoquinoline-l-acetamides 195 (R = H) with 36% aqueous CH20 gave 1,3,4,6,7,11 b-hcxahydro-2//-pyrirmido[6,1 - ]isoquinolin-2-oncs 153 and their 3-methyl derivatives <1997LA1165>. When the reaction was carried out in the presence of 37% aqueous NaOH, 3-hydroxymethyl derivatives 152 were obtained. Reactions with PhCHO were stereospecific affording only diastereomers 196 (Equation 41). 

AW, Acid-washed Choi, Cholesterol DMAP, 4-(Dimethylamino)pyridine DMF, N,/V-Dimethylformamide DMTr, Di(p-niethoxyphenyl)phenyl methyl GalNAc, N-Acetylgalactosamine, 2-acetamido-2-deoxy-D-galactose HMF, 5-Hydroxymethylfur-fural, 5-(hydroxymethyl)-2-furaldehyde INOC, Intramolecular nitrile oxide-alkene cycloaddition Lea, Lewisa Lex, Lewisx MOM, Methoxymethyl MP, p-Methoxyphe-nyl MS, Molecular sieves NIS, N-Iodosuccinimide PCC, Pyridinium chlorochromate PDC, Pyridinium dichromate PMA, Phosphomolybdic acid PMB, p-Methoxybenzyl ... 

Metabolites that contain pyridoxol (2-methyl-3-hydroxy-4,5-di[hydroxymethyl]pyridine), the water-soluble vitamin B6. Phosphorylated forms of pyridoxal (the aldehyde form) and pyridoxamine (the amino form), known respectively as pyridoxal 5-phosphate (PLP) and pyridoxamine 5-phosphate (PMP), are tightly-bound coenzymes. 

Anilinomethyl-glucoimidazole (129) (5tf,6/ ,7S,SS)-5-(Hydroxymethyl)-2-(phenylamino)methyl-5,6,7,8 -tetrahydro-imidazo [ 1,2-a] pyridine- 6,7,8-triol... 

Hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl[2S,3S.8aR]-5-oxo-5H-oxazolo[3.2-a]pyridine 5H-Oxazolo[3,2-a]pyridin-5-one, hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-, [2S-(2a,3p,8ap)]- (12) (116950-01-7) (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol 1,3-Propanediol, 2-amino-1 -phenyl (9) (3306-06-7)... 

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