ISOQUINOLINES .7. REACTION OF ETHYLENE-OXIDE WITH ISOQUINOLINES - NOVEL ISOQUINOLONE AND OXAZOLIDINE FORMATION

Aprotic deamination of 3-amino-l-bromo-4-nitrophenylisoquinoline (6) followed by partial reduction yielded 4-aminophenyl-l-bromoisoquinoline (8), and complete reduction yielded 4-aminophenylisoquinoline (9). Isoquinolines 8 and 9 when treated with excess ethylene oxide in acetic acid afforded 4-[p-bis(2-hydroxyethyl)amino]phenyl-2-(2-hydroxyethyl)-l-isoquinolone (15a) and 2-(2-acetoxyethyl)-4-[p-bis(2-hydroxyethyl)amino]phenyl-l-isoquinolone (15b). Evidence for a mechanism involving an oxazolidine intermediate is presented. When isoquinoline (17) was similarly treated with ethylene oxide, 2, 3-dihydro-10bH-oxazolo[2, 3-a]isoquinoline (19) was obtained. © 1978, American Chemical Society. All rights reserved.