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Synthesis and Nucleophilic Reactions of Cyano Substituted N ‐Methoxyisoquinolinium Salts
Author(s) -
Heber Dieter,
Holzgrabe Ulrike,
Werra Wolfgang
Publication year - 1993
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19933261004
Subject(s) - chemistry , nucleophile , medicinal chemistry , iminium , isoquinoline , hemiaminal , amine gas treating , derivative (finance) , salt (chemistry) , nucleophilic substitution , polymer chemistry , stereochemistry , organic chemistry , ion , financial economics , economics , catalysis
Starting from isoquinoline, the cyano substituted N ‐methoxyisoquinolinium salts 1.1 and 1.4 are prepared. Their behaviour in the presence of O‐, C‐ and N‐nucleophiles in different aprotic solvents is examined: from the 1‐cyano substituted isoquinolinium derivative 1.1 , 1‐ and 3‐animals or 1‐iminium salts are obtained depending on the amine used, and N ‐methoxyisocarbostyril 4.1.1 in H 2 O and OH − . The reaction of the 4‐cyano‐ N ‐methoxyisoquinolinium salt 1.4 with amines yields 1‐aminals and with OH − the corresponding hemiaminal. Conversion with CN − results in dinitrile derivatives and N ‐oxides.