Synthesis of 1, 6-disubstituted 2, 4-pyridinediones from 5-acetoacetyl-2, 2-dimethyl-1, 3-dioxane-4, 6-dione

DB Rubinov, TA Zheldakova, IL Rubinova

Index: Rubinov; Zheldakova; Rubinova Russian Journal of Organic Chemistry, 2004 , vol. 40, # 9 p. 1329 - 1331

Full Text: HTML

Citation Number: 6

Abstract

Abstract 5-Acetoacetyl-2, 2-dimethyl-1, 3-dioxane-4, 6-dione reacts with aliphatic amines and p-methoxy-aniline to afford the corresponding 5-[3-alkyl (or aryl) amino-2-butenoyl] derivatives. Heating of the latter in boiling toluene gives 86–90% of N-substituted 6- methylpyridine-3-carboxylic acids which undergo decarboxylation in diethylene glycol dimethyl ether at 160° C, leading to N-substituted 6-methyl-1, 2, 3, 4-tetrahydro-pyridine-2, ...