Site-selective formation of N-arylmethylimidazoles and C-arylimines in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with aromatic aldehydes |
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Authors: | Akihito Saitoh Koichi Suzuki Maki Kasahara Taisuke Matsumoto |
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Institution: | a Advanced Device Technology Development Center, Canon Inc., 3-30-2, Shimomaruko, Ohta-ku, Tokyo 146-8501, Japan b Institute for Materials Chemistry and Engineering, Kyushu University, 6-1, Kasuga-koh-en, Kasuga 816-8580, Japan |
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Abstract: | Regioselective formation of N-arylmethylimidazoles and C-arylimines was found in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with selected aromatic aldehydes. The regiochemistry of the reaction products was confirmed by single crystal X-ray analysis. Gibbs free energy calculation using DFT method at the B3LYP/6-31G(d) level supports the regio-selectivity observed. The 4-imine obtained in the reaction of 4,5-diamino-2,1,3-benzothiadiazole with pyrene-1-carboxaldehyde showed an unusually low magnetic field shift of the imine proton that was reproduced by molecular calculations. |
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Keywords: | Thiadiazole Regioselective formation Chemical shift B3LYP/6-31G(d) |
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