Reactions of Quinolines and Isoquinolines Flashcards
selective reduction of nitrogen ring
uses H2/Pt, 2atm and water
Ring oxidation
using Pd/C and MeCN at 100C oxidises to aromatic ring
N-oxide formation
quinoline and m-CPBA
reduction of N-oxides
using PCl3 gives quinoline, driving force is formation of PO bond
EAS of quinoline n-oxides
substitution at quinoline C4, most resonance forms
Installing Cl leaving group in quinoline
N-oxide and POCl3 adds Cl at C2 position
Installing Cl leaving group in isoquinoline
N-oxide and POCl3 adds Cl at C1 to preserve aromativiet
Conversion to iso/quinolone
N-oxide with Ac2O and heat then NaOH
EAS
substitution at electron rich benzene, more wheland intermediates, more stable and more aromaticity preserved
side chain chemistry
C2 and C4 quinoline side chains are acidic and can be deprotonated
selective reduction of benzene ring
H2/Pt, 3 atm and conc H+