Pyrimidine derivatives XII. A convenient preparation of 6-formylpyrimidinedione and 2- and 3-formylpyridine derivatives from corresponding nitrooxymethyl derivatives

Article abstract of DOI:10.1002/jhet.5570310654

The convenient preparation of 6-formylpyrimipinedione derivatives and 2- and 3-formylpyridine are described. Thus, 5-bromo-1,3-dimethyl- (1a), 5-bromo-3-methyl-1-(2-nitrooxyethyl)- (1b), and 5-bromo-3-methyl-1-(3-nitrooxypropyl)-2,4(1H,3H)-pyrimidine-dione (1c) were converted to the corresponding 6-formyl compounds 2a, 2b, and 2c, respectively, in excellent yields by the reaction with triethylamine and 1,4-diazabicyclo[2.2.2]octane. These 6-formylpyrimidinedione derivatives are key intermediates for the preparation of 6-carbon-carbon substituted compounds, which are expected to be potential antitumor and antiviral agents. Similarly, 2-(and 3-)formylpyridine (9a (and 9b)) were obtained by the reaction of 2-(and 3)nitrooxymethylpyridine (8a (and 8b)) with 1,4-diazabicyclo[2.2.2]octane.