I. Bata et al., REDUCTIVE FORMATION OF 3-BENZOYLAMINOPYRROLO[2,1-A]ISOQUINOLINES FROM1-[(1,2,4-OXADIAZOL-3-YL)ETHYL]ISOQUINOLINES, ACH, models in chemistry, 131(3-4), 1994, pp. 351-362
Catalytic hydrogenation of diazol-3-yl)ethyl]-1,2,3,4-tetrahydroisoqui
nolines (9) gave 3-benzimidopyrrolo[2,1-a]isoquinolines (11) by reduct
ive cleavage of the N-O bond of the oxadiazole ring and subsequent eli
mination of ammonia. A mixture of 3-benzamidopyrrolo[2,l-a]isoquinolin
e (18) and 11 was formed from the corresponding 3,4-dihydroisoquinolin
e derivatives (16) in a similar route.