115879-54-4Relevant articles and documents
Azafluorenes Containing Two Bridgehead Nitrogen Atoms
Jones, Terence R.,Rose, Francis L.
, p. 2585 - 2592 (2007/10/02)
Four new tricyclic cationic ring systems containing two bridgehead nitrogen atoms have been synthesised: pyridoimidazopyridinium, pyridoimidazopyridinium, pyridoimidazopyrazinium, and pyridoimidazothiazolium.In the case of the first named system the parent heterocycle has been prepared.A new, efficient synthesis of the previously described imidazodipyridinium cation is also noted.The synthetic route to these compounds involved N-alkylation of an azinol with 2-chloromethylpyridine and ring closure of the resulting lactam with phosphoryl chloride.In the case of uracil and 6-methyluracil N-alkylation was proved to have occured at N-1 by unambiguous synthesis.Nucleophilic attack by hydroxide ion upon the 1,3-dimethylpyridoimidazopyridinium cation led to 3-(2-acetylaminoprop-1-enyl)imidazopyridine the structure of which was confirmed by unambiguous synthesis of its hydrolysis product.
