99758-10-8Relevant academic research and scientific papers
Reaction of Aromatic N-Oxides with Dipolarophiles. VIII. Carbamation Products of 2-Anilinopyridine Derivatives
Hisano, Takuzo,Harano, Kazunobu,Matsuoka, Toshikazu,Suematsu, Fumihiro,Ohizumi, Norihide
, p. 1869 - 1877 (2007/10/02)
In the 1,3-dipolar cycloaddition reaction of pyridine N-oxides with phenyl isocyanates, we have isolated 1,5-sigmatropy products of the primary cycloadduct and carbamation products of 2-anilinopyridines.In connection with the tautomerism of 2-anilinopyridines, the structure of the carbamation products is discussed in detail based on kinetic, molecular orbital calculation and spectral data.A comparison of the spectral data with those of structurally related compounds indicated that the carbamation does not occur at the ring nitrogen but at the exocyclic one.Keywords -- tautomerism; 2-anilinopyridine; molecular orbital theory; carbamation; phenyl isocyanate; 2-pyridone-imine; 1,3-dipolar cycloaddition; pyridine N-oxide; 2-(N-phenylcarbamoylanilino)pyridine
