112010-92-1Relevant articles and documents
Hydroxyiminoisoquinolin-3(2H)-ones. Part 7. Rearrangement of 4-Hydroxyimino-1,4-dihydroisoquinolin-3(2H)-ones under Wolff-Semmler-Type Reaction Conditions
Tikk, Istvan,Deak, Gyula,Sohar, Pal,Tamas, Jozsef
, p. 1101 - 1119 (2007/10/02)
The refluxing of 1-aryl-4-hydroximino-1,4-dihydroisoquinolin-3(2H)-ones (1 a-e) with Beckmann's mixture (AcOH/Ac2O/HCl) resulted in a hitherto unknown rearrangement to give 4-acetylamino-1-arylisoquinolin-3(2H)-ones (2 a-e).At 55 deg C, the 6,7-dimethoxy derivatives (1c) and (1d) yielded 3,4-dioxo-1-phenyl-1,2,3,4-tetrahydroisoquinolin-1-ol (6) and its N-methyl derivative (7), respectively.Reduction of these compounds with sodium borohydride caused cleavage of the hetero ring to give the acid amides (8) and (9).From the reactions at 95 deg C of the 6,7-dimethoxy derivative (1d) the oxazoloisoquinoline (10) was isolated.