Abstract
AbstractPhosphane‐free Pd0‐catalyzed intramolecular aromatic amination was studied. o‐Halophenethylamines and 3‐(o‐halophenyl)propylamines were found to be transformed into indolines and quinolines in a catalytic system based on Pd(OAc)2 and Cu(OAc)2 in the presence of K2CO3. Application of the method to substrates containing isoquinoline rings – the 1‐(o‐bromobenzyl)‐3,4‐dihydroisoquinolines 6, the 1‐(o‐bromobenzyl)‐1,2,3,4‐tetrahydroisoquinolines 7, and the 1‐(o‐bromophenethyl)isoquinolines 9 – provided the indolo[2,1‐a]isoquinoline and dibenzo[a,f]quinolizine ring systems 8 and 10. Extension of the method to β‐carbolines (compounds 11, 12, and 17) produced the benz[f]indolo[2,3‐a]indolizine‐13‐ones 15 and the benz[f]indolo[2,3‐a]quinolizine 18. The benzo[f]pyrido[3,4‐a]indolizine and indolo[f]pyrido[3,4‐a]indolizin‐12‐one ring systems 27 and 31 were built in a similar manner. It was also found that under an atmosphere of CO the same catalytic system produced the corresponding benzolactams, the isoquino[2,1‐a][2,7]naphthyridine 34 and the indolo[2,3‐a]pyrido[g]quinolizin‐8‐one 36 [(±)‐dihydronaucléfine] in good yields.
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call