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Nitration of 5,6,7,8‐tetrahydro‐5,8‐methanoisoquinoline N ‐oxide with other aromatic substitutions. Isolation and mutagenicity of an α‐nitropyridine N ‐oxide
Author(s) -
Tanida Hiroshi,
Irie Tadashi,
Wakisaka Yoshiharu
Publication year - 1986
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.5570230136
Subject(s) - nitration , chemistry , oxide , deoxygenation , nitric oxide , medicinal chemistry , nitro , derivative (finance) , organic chemistry , catalysis , alkyl , financial economics , economics
Treatment of 5,6,7,8‐tetrahydro‐5,8‐methanoisoquinoline N ‐oxide ( 2 ) with fuming nitric acid afforded 3‐nitro‐5,6,7,8‐tetrahydro‐5,8‐methanoisoquinoline N ‐oxide ( 3 ), an example of formation of an α‐nitropyridine N ‐oxide derivative by nitration of N ‐oxides. Further reaction of 3 resulted in deoxygenation giving 3‐nitro‐5,6,7,8‐tetrahydro‐5,8‐methanoisoquinoline ( 4 ). No aromatic nitration was observed by similar treatment of 5,6,7,8‐tetrahydro‐5,8‐methanoisoquinoline ( 1 ) or 5,6,7,8‐tetrahydroisoquinoline N ‐oxide ( 11 ). Some other aromatic substitutions with 1 and 2 were caried out to obtain mainly the 3‐substituted derivatives. Significant mutagenicity of 3 is briefly reported.