Reaction of ketone enolates with 2, 4-dichloropyrimidine. A novel pyrimidine to pyridine interconversion
…, DR Carver, JS Hubbard, YP Sachdeva…
文献索引：Bell, Harold M.; Carver, David R.; Hubbard, James S.; Sachdeva, Yesh P.; Wolfe, James F.; Greenwood, Thomas D. Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3442 - 3444
Treatment of 2, 4-dichloropyrimidine (1) with a series of ketone potassium enolates in liquid NH3 results in a novel ring transformation leading to the formation of 6-(cyanamino) pyridines (8a-c). An SN (ANRORC) mechanism initiated by nucleophilic addition of the enolate to C6 of 1 is proposed. The pyrimidine-pyridine transformation involves displacement of the N,-C2-N3 portion of pyrimidine with a CCN moiety, where the enolate ...
