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Sels de N ‐alcoxyquinoléinium et de N ‐alcoxyisoquinoléinium porteurs d'une fonction ester dans leur chaine alcoxyle: Synthèse et réactivité vis‐a‐vis des ions cyanure
Author(s) -
Sliwa Henri,
RandriaRaharimanana Clarisse,
Ouattara Lassina
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270328
Subject(s) - chemistry , quinoline , medicinal chemistry , isoquinoline , cyanide , perchlorate , aqueous solution , potassium cyanide , salt (chemistry) , cyanide ion , ion , inorganic chemistry , organic chemistry
Abstract Reaction of ethyal α‐bromoisobutyrate on quinoline 1‐oxide and isoquinoline 2‐oxide in the presence of silver perchlorate leads to the corresponding N ‐alkoxyl salts 1 and 2 . On treatment with potassium cyanide, these salts are converted into 2‐cyanoquinoline and 1‐cyanoise‐quinoline according to mode B of the Katritzky' s classification concerning the reaction of nucliophiles on N ‐alkoxypyridinium salts. When the reaction of cyanide ions were performed on salt 1 at 0° in aqueous solution the dihydro aromatic 4 was isolated. This result confirms the addition‐elimination mechanism of the reaction studied.