Pyridone benzoyl chloride

Acoxyl-2(lH)-pyridones. Benzoyl chloride added slowly at room temp, to 2-ethoxypyridine N-oxide l-benzoyloxy-2(lH)-pyridone. Y 93%. F. e. s. L. A. Paquette, Am. Soc. 87, 1407 (1965) peptide synthesis with 2-ethoxypyridine... 

The alkylation of 4-hydroxypyrimidines (60) has also been studied. The results are readily explicable by the HSAB principle. Acetylation of the thallium(I) salt of 2-pyridone (61) at —40° provides up to 40% of the A -acetyl derivative, which on warming rearranges largely to the O-isomer. The Na salt of phenanthridinone reacts with benzoyl chloride at room temperature to afford only the less stable 0-benzoylated product (62). 

Acetyl or benzoyl chloride and 2-picoline-1-oxide in nonaqueous solvents give the acetate or benzoate of 2-pyridinemethanol and a small amount of 2-pyridylmethyl chloride " Pyridine-1 -oxide and tosyl chloride in benzene give 2,3-dipyridyl ether, AT-(2 -pyridyl)-2-pyridone, A -<2 -pyridyl)-5-chloro-2-pyri-done, A (2 -pyridyl)-3-chloro-2-pyridone, and 3-tosyloxypyridine. Tracer studies have suggested that the 3-tosyloxypyridine is formed via an intimate ion pair (xn-443). (For alternate suggestion, see Ch. I). 

Among dichloro bis-electrophiles, malonyl chloride with enamine 183b affords pyridone 189, probably resulting from C-alkylation and cyclocondensation followed by aromatization (02T2821). Finally, o-chloro-benzoylchloride leads to C-benzoylation and subsequent intramolecular substitution of the isolable intermediate to yield quinoline 190 (03ARK (is.2)146). 

---