The reaction of 1‐(hydrazidomethyl)‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline 3 with aromatic aldehydes yield hydrazones 4a,b or pyrimido[6,1‐a]isoquinolines 5a‐c depending upon the proportions of the reagents. With ketones, 3 gives only hydrazones 4a‐d and 7, which can be transformed to pyrimidoisoquinolines 10a‐e and 11 with aldehydes. The ring closures are stereospecific; the relative configurations were determined by DNOE measurements.
ASJC Scopus subject areas
- Organic Chemistry