ChemInform Abstract: Bromination of Isoquinoline, Quinoline, Quinazoline and Quinoxaline in Strong Acid.

Abstract

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Iodination of Isoquinoline by Trifluoromethanesulfonic Acid

“…The representative datas are summarized in Table 1. According to above literatures, [10] we know that acid plays an important role in halogenation. On the one hand, isoquinoline ( 1 a ) was deactivated by N ‐protonation which leading to higher electrophilic attack selectivity between the 5‐position and the 8‐position.…”

“…In sharp contrast, the iodination reaction of isoquinoline heteroarenes is underdeveloped. In 2002, Gouliaev reported isoquinoline was regioselectively monobrominated in concentrated H 2 SO 4 or CF 3 SO 3 H which used NBS or N , N’ dibromoisocyanuric acid (DBI) as the halogen source [10] (Scheme 1a). In the same year, Denny group described the synthesis and structure‐activity relationships for related heterocyclic derivatives of Tetracyclic Phenazines which iodoisoquinolines was key intermediate during the synthesis process [11] (Scheme 1b).…”