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Investigations on the Pathway of the Fluorescence Reaction of a Pharmaceutically Important 1,3‐Diamine with 2‐Benzoylbenzaldehyde

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‐benzoylbenz[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”.