494-19-9, Name is Iminodibenzyl, molecular formula is C14H13N, Application In Synthesis of Iminodibenzyl, belongs to pyrrolines compound, is a common compound. In a patnet, author is Rostovskii, Nikolai, V, once mentioned the new application about 494-19-9.
Acid-catalyzed rearrangement of 1-acyl-2-azabuta-1,3-dienes to 4-pyrrolin-2-ones
1-Acyl-2-azabuta-1,3-dienes underwent rearrangement to 4-pyrrolin-2-ones in the presence of acidic catalysts (silica gel or ZnCl2) and water. The reaction proceededviathe formation of 2,3-dihydroxy-3,4-dihydropyrrole and 2-hydroxy-2H-pyrrole intermediates, the latter of which was transformed by [1,5]-sigmatropic shift of carbonyl substituent and prototropic isomerization. 4-Chloro-substituted 1-acetyl-2-azabuta-1,3-dienes were stable toward rearrangement, while brominated analogs rearranged into 4-pyrrolin-2-ones, probably as a result of the initial radical hydrodebromination. According to calculations performed at the DFT level, two steps of the reaction were catalyzed by acid: the cyclization of 2-azabutadiene and the sigmatropic shift in the 2-hydroxy-2H-pyrrole intermediate.
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Reference:
Pyrroline – Wikipedia,
,1-Pyrroline | C4H7N – PubChem