Mechanism of the condensation reaction between 1-aryl- and heteroaryl-1,4-dihydro-3(2H)-isoquinolinones and aldehydes |
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Authors: | L szl Hazai,Gyula De k,J zsef Tam s,G bor Doleschall,Gabor T th |
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Affiliation: | László Hazai,Gyula Deák,József Tamás,Gábor Doleschall,Gabor Tóth |
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Abstract: | 4-Benzylidene-1-phenyl-1,4-dihydro-3(2H)-isoquinolinone, the intermediary product of the carbonyl condensation reaction between 1-phenyl-1,4-dihydro-3(2H)-isoquinolinone and benzaldehyde, rearranges in the presence of an equivalent quantity of sodium hydride into 4-benzyl-1-phenyl-3(2H)-isoquinolinone. As the possibility of the migration of the hydrogen at C-1 in the form of a proton or a hydrogen atom (radical reaction) was excluded, the mechanism of the rearrangement could be depicted as an intermolecular hydride anion migration. In case of the 1-(4-pyridyl)- and 1-(3-pyridyl)-1,4-dihydro-3(2H)-isoquinolinones, however, the rearrangement can be carried out also in polyphosphoric acid and in this case a proton loss-proton gain mechanism was proved. |
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