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Unexpected formation of 1,2‐dihydro‐2‐azolyl‐and azinylisoquinolines by the reduction of the corresponding isoquinolinium salts with sodium borohydride in methanol
Author(s) -
Prauda Ibolya,
TóthLauritz Mária,
Reiter József
Publication year - 2004
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.5570410611
Subject(s) - chemistry , sodium borohydride , moiety , methanol , ring (chemistry) , medicinal chemistry , sodium , borohydride , organic chemistry , catalysis
The reduction of different 2‐azolyl‐and azinylisoquinolinium salts with sodium borohydride in methanol was studied. Surprisingly, contrary to what is found in the literature 1,2‐dihydroisoquinoline derivatives were obtained. Their formation was attributed to the electron withdrawing character of the heterocyclic ring in position 2 of the isoquinolinium moiety. This was corroborated by synthesis and reduction of differently substituted 2‐phenyl‐ and 2‐methylisoquinolinium salts.