Heterocycles in organic synthesis. Part 25. Reagents for the conversion of halides into aldehydes and ketones
Abstract
The sodium salts of 1-hydroxy-4,6-diphenyl-2-pyridone, 3-hydroxy-2-phenyl-4(3H)-quinazolinone, and 2-benzenesulphonamidopyridine 1-oxide react with alkyl and benzyl halides to give crystalline N-alkoxy- and N-benzyloxy-derivatives. The latter undergo thermolysis and photolysis to aromatic aldehydes and ketones in high yields. N-Alkoxy-analogues similarly yield aliphatic carbonyl compounds but these are contaminated by significant amounts of the corresponding alcohol.