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Mechanism of the condensation reaction between 1‐aryl‐ and heteroaryl‐1,4‐dihydro‐3(2 H )‐isoquinolinones and aldehydes
Author(s) -
Hazai László,
Deák Gyula,
Tamás József,
Doleschall Gábor,
Tóth Gabor
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220606
Subject(s) - chemistry , benzaldehyde , condensation , hydride , medicinal chemistry , aryl , proton , sodium hydride , hydrogen atom , stereochemistry , hydrogen , organic chemistry , catalysis , physics , alkyl , quantum mechanics , thermodynamics
Abstract 4‐Benzylidene‐1‐phenyl‐1,4‐dihydro‐3(2 H )‐isoquinolinone, the intermediary product of the carbonyl condensation reaction between 1‐phenyl‐1,4‐dihydro‐3(2 H )‐isoquinolinone and benzaldehyde, rearranges in the presence of an equivalent quantity of sodium hydride into 4‐benzyl‐1‐phenyl‐3(2 H )‐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(2 H )‐isoquinolinones, however, the rearrangement can be carried out also in polyphosphoric acid and in this case a proton loss‐proton gain mechanism was proved.