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Synthesis and nitration of some thieno-fused analogues of the benzo[a]quinolizinium cation
Authors:Kiyoshi Sato  Sadao Arai  Takamichi Yamagishi
Abstract:Three thieno-fused analogues of benzoa]quinolizinium ( 1 ), thieno3,2-a]- and thieno2,3-a]quinolizinium 4 and 5 and thiazolo2,3-a]isoquinolinium ( 6 ), were synthesized by photocyclization of 1-(2-thienylvinyl)pyridinium salts 9a and 9b and 3-styrylthiazolium salt 9c , respectively. The nitration of the compounds 4, 5 , and 6 occurred predominantly at positions 2, 3, and 7, respectively, while the nitro group was introduced into the 8- and 10-positions of 1 in the ratio of 68:32. The nmr and uv spectral properties and reduction potentials of 4–6 were also compared with those of the parent compound 1 .
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