Journal of the Chemical Society. Perkin transactions I p. 2617 - 2621 (1983)
Update date:2022-08-04
Topics: Nucleophilic Displacements
Katritzky Alan R.
Agha, Bushra J.
Awartani, Radi
Patel, Ranjan C.
Heteroarylamines and the appropriate pyrylium salts give 1-heteroaryl-2-ethoxycarbonyl-4,6-diphenylpyridinium, and 1-(2-pyridyl)-2,6-diethoxycarbonyl-4-phenylpyridinium salts.Hydrolysis and decarboxylation afford 1-(2-pyridyl)-2,4-diphenyl- and 1-(2-pyridyl)-4-phenyl-pyridinium salts.Neither these, nor their 2,4,6-triphenyl analogues underwent smooth nucleophilic substitution. 1-Pyrimidin-2-yl- and 1-(4,6-dimethylpyrimidin-2-yl)-2-ethoxycarbonyl-4,6-diphenylpyridinium with ethanolic NaOEt smoothly formed the corresponding pyrimidin-2-ones via intramolecular attack.
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