THE OXIDATION OF SOME β-SUBSTITUTED PYRIDINE ALKIODIDES¹

Bromination of 1-alkyl-3-methyl-2-pyridones with N-bromosuccinimide

“…In concentrated reaction mixtures significant yields of ring bromination occurred even in the presence of dibenzoyl peroxide. The 1-methyl derivative, 5, was more sensitive to this concentration effect than was the l-benzyl-3-methyl-2-pyridone (8). By a proper choice of reaction conditions selectivity could be controlled to give crude products which crystallized and whose NMR analyses showed less than 10% contamination by the isomeric bromination product.…”

“…To a solution of 6.44 g of 87% KOH in 150 ml of absolute ethanol at 50 °C was added 3-methyl-2pyridone. 8 The resulting solution was stirred for 20 min before the dropwise addition of benzyl chloride. The mixture was stirred at 50 °C for 3 h, concentrated under reduced pressure, poured into 180 ml of water, and extracted with chloroform (3 X 50 ml).…”

Kinetics and mechanism of the oxidation of heteroaromatic cations by ferricyanide ion

“…II. 6 Data in parentheses based on log (kp/kp) = -0.33 + 0.36, which is derived from the correlations lines in Figure 6. This data is more reliable than kp/kp based on Table II since kp values for X = 4-CH30 and H in Table II have relatively large experimental errors.…”

“…One possibility is that this species is hexacyanohydridoiron(III), which involves a 7-coordinate Fe(III) complex. Several stable 7-coordinate Fe(III) complexes are Figure 6. Energy profiles for the rate-determining step in the oxidation of isoquinolinium cations by Fe(CN)63-.…”

Oxidation of 1-(3,4-Dimethoxyphenethyl)-3-ethyl-4-(carboxaldehyde diethylacetal)pyridinium Bromide by Potassium Ferricyanide

“…However, when the 3-substituent is methyl, ethyl, or bromo, pyridone formation occurs at the 2-position exclusively. 7…”