H. Tanida, T. Irie, Y. Wakisaka
1986
Citations
0
Influential Citations
9
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
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.