Ring opening and ring contraction in reactions of some aminobromo‐ and dibromoisoquinolines with potassium amide in liquid ammonia
- 1 January 1974
- journal article
- abstracts
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 93 (11) , 298-300
- https://doi.org/10.1002/recl.19740931109
Abstract
Reactions 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.Keywords
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