Investigations on the pathway of the fluorescence reaction of a pharmaceutically important 1,3-diamine with 2-benzoylbenzaldehyde

Article abstract of DOI:10.1002/ardp.19963290508

The reaction of 2-benzoylbenzaldehyde (1) with primary diamine 2, generated by rearrangement and hydrolysis of Oxazepam, in CD₃OD leads to intensely fluorescing deuterated isoindoloquinazolines 3 and 4. Reduction of ethyl 2-benzoylbenzoate (5) with LiAlD₄ followed by oxidation with MnO₂ yields 2-benzoyl-benz[D]aldehyde (7). The condensation of 7 with diamine 2 leads to isoindoloquinazoline 12, free of deuterium. On the basis of these experiments a plausible pathway is proposed for the 'fluorescence reaction'.