Studies on ketene and its derivatives. CI. Reaction of diketene with 4-amino-methylpyridine 1-oxides.

DOI DOI Web Site Open Access

Search this article

Description

The reaction of diketene with 4-amino-methylpyridine 1-oxides was examined. 4-Aminopyridine 1-oxide (1a) and 4-amino-3-methylpyridine 1-oxide (1c) reacted with diketene in the presence of triethylamine at 0--5° to give the corresponding substituted 2, 6-dimethyl-4-pyrone-3-carboxamides ; i. e., N-(1-oxido-4-pyridyl) (3a) and N-(3-methyl-1-oxido-4-pyridyl) (3c) compounds. The reaction of diketene with 4-aminomethylpyridine 1-oxides (1b, d, and e) afforded 4-acetoacetamindopyridine 1-oxides (2b, d, and e) under the same conditions. However, the reaction of diketene with 4-aminopyridine 1-oxides (1f and g) possessing an ethyl group at the 3-position gave N-(3-ethyl-1-oxido-4-pyridyl)-2-acetyl-3, 5-dimethyl-phenol-4-carboxamides (5f and g), together with N-(3-ethyl-1-oxido-4-pyridyl)-2, 6-dimethyl-4-pyrone-3-carboxamides (3f and g). The mechanism of formation of compounds 5f and g is discussed.

Journal

Keywords

Details 詳細情報について

Report a problem

Back to top