並列摘要
Nitration of dimethyl 2-aminoazulene-1,3-dicarboxylate (I) with nitric acid in acetic acid at room temperature gave five products . They were identified by spectroscopic methods, in which compound (V) is the first obtained in the nitration process as substituted at 4 position. Meanwhile in this reaction the yield of the major compound (II) was increased as reaction temperature raised. It is considered to be obtained under thermodynamic control condition. On the other hand, when nitration was carried out with cupric nitrate in acetic anhydride at -78 °C, compound (IV) was obtained as the major product, which has been considered as the kinetic control one. Due to the steric hindrance effect from S-isopropyl, the nitration of dimethyl 2-amino-Sisopropylazulene-1,3-dicarboxylate (VII) with cupric nitrate gave predominantly 6-nitro product without 4 position nitration product. Another nitration of 2-amino-l .3-dicyanoazulene (XI) with cupric nitrate gave 6-nitro-2-amino-1,3-dicyanoazulene predominantly and a deamination 6-nitro product.
延伸閱讀
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