Abstract
AbstractReactions of some aminobromo‐ and dibromoisoquinolines with KNH2 in liquid NH3 have been investigated. Compounds with an amino group and a bromo atom in positions α to the heteroatom, show a very fast ring opening, leading to o‐cyanobenzyl cyanide. The 1,4‐substituted aminobromoisoquinolines do not react; 4‐amino‐3‐bromoisoquinoline undergoes ring opening into o‐cyanobenzyl isocyanide, 3‐amino‐4‐bromoisoquinoline ring contraction to 1‐cyanoisoindole. The dibromoisoquinolines react primarily by nucleophilic substitution.
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