Pyridine hydroxymethyl

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. 

Several of these steroid derivatives underwent elimination of phosphorodichloridate anion, giving hydrocarbon products, rather than ester formation when treated with methanolic pyridine. Pyrophosphoric acid itself has been used to phosphorylate (2-hydroxymethyl)pyridine. ... 

Finally, we also mention a cobalt ring (37), and the non-magnetic ring Zn C [Zn(hmp)2]6 2+ analogue (38), in which hmp is 2-hydroxymethyl-pyridine. A central octahedral Zn2+ ion is encapsulated in a hexanuclear ring. 

Fig. 21. Schematic and packing excerpt illustrations of the principal H-bond interactions found in the salt-type associates of 7B0> (the bold H stands for host, G for guest H-bonds as broken lines O atoms dotted N atoms hatched H atoms connected with non-heteroatoms are shown as sticks only). The 7 2-(hydroxymethyl)pyridine (1 1) associate follows nearly the same principle as shown for type I...

Dihydroxy-2-hydroxymethyl-pyridin reagiert mit verschiedencn Diazonium-Salzen. Die Produkte lassen sich durch Methylierung mit Diazomethan zu den entsprechenden 2-Azopyridin-Derivaten isomerisieren4 ... 

The side chain in fluorinated 2-(hydroxymethyl)pyridines is selectively oxidized using manganese dioxide, giving the corresponding pyridine-2-carbaldehydes 4.259... 

Method A. To a solution of substituted 2-(hydroxymethyl)pyridine in CHC12, Mn02 (2-3 x wt of substrate) was added. The mixture was refluxed for 2 h while stirring, filtered and the Mn02 cake was washed well with boiling CHC13. The CHC13 extracts were combined, dried (MgS()4), and distilled to furnish the aldehydes. In the case when the aldehyde was a solid after evaporation of the CIICI,. it was crystallized from petroleum ether yields 3-F, 41 % 5-F, 39%. 

Method B Pb(OAc)4 (1.1 wt equiv) was added portionwise to the 2-(hydroxymethyl)pyridine (1 wt cquiv) dissolved in dry CHC13. The yellow solution was allowed to stand for 3 d at rt, then treated with excess KHS03 soln, and filtered. The organic layer was separated, dried (MgS04), and distilled to give the pure aldehyde yields 5-CF3. 52% 5-OCF3, 59%. 

Scrimin and co-workers have extensively studied the ester-cleavage abilities of various Cu(II)-chelating bidentate ligand [(2-hydroxymethyl)pyridine] amphi-phile, 9, and related bolaphile, 10, in micellar media [32], The corresponding metallomicelles are powerful catalysts for the cleavage of substrates, e.g. p-nitrophenyl alkanoates, that do not coordinate with the metal-complex core. Subsequent studies demonstrated that tridentate ligand amphiphiles such as 9,... 

Fig. 3.11 Initial synthesis of 3,4-dimethoxy-2-hydroxymethyl-pyridine as a building block for pantoprazole.

The 3,4-dioxoperhydro derivative of (3) was obtained by cross carbonylation of 2-hydroxymethyl-pyridine <87CC125>. Reaction of Schiff bases, prepared from 2-aminopyridine and its 5,6-benzologue with aldehydes and dichlorocarbene, afforded 2-aryl-3-chloro-4-oxo-4/f derivatives of (12) and its 6,7-benzologue <9lKGS8io>. 

Figure 18 Calculated (bottom) and simulated (top) powder diffractograms of 5-bromo-2-(hydroxymethyl)pyridine. ...

Reaction of 2-fluoro-3-trifluoromethylfurans 235 with allyl alcohols followed by Claisen rearrangement directly produced butenolides 237 [145, 146]. Oppositely, allyl mercaptane formed stable substitution product 236 [146], A similar transformation was reported for benzyl alcohols. While benzhydryl and (2-thienyl)methyl groups migrated at room temperature directly furnishing butenolides 239, in the case of benzyloxy derivatives, heating at 120 °C was required to reach the transformation. On the other hand, stable up to 140 °C products 238 were formed in the reaction of benzylamine, benzyl mercaptane, and 2-(hydroxymethyl)pyridine [147]. 

---