W. Brown, A. Gouliaev
Aug 4, 2004
Citations
0
Influential Citations
21
Citations
Journal
Synthesis
Abstract
Bromination of benzazines and benzodiazines most often gives a mixture of products. In this paper, we show that isoquinoline (1) may be regioselectively monobrominated in concentrated H 2 SO 4 using NBS or in CF 3 SO 3 H using N,N'-dibromoisocyanuric acid (DBI) to give 5-bromoisoquinoline (2). The bromination was found to be highly sensitive to the choice of brominating agent, acid, temperature and concentration. Quinoline, quinazoline and quinoxaline may be brominated likewise, although with the strong regioselectivity reserved to isoquinoline.