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The novel transition metal free synthesis of 1,1′-biazulene |
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| Authors: | Taku Shoji Shunji Ito Masafumi Yasunami |
| Affiliation: | a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan b Department of Frontier Materials Chemistry, Faculty of Science and Technology, Hirosaki University, Hirosaki 036-8561, Japan c Department of Materials Chemistry and Engineering, College of Engineering, Nihon University, Koriyama 963-8642, Japan |
| Abstract: | Reaction of 1-azulenyl methyl sulfoxide (1) under acidic conditions gave the 1,1′-biazulene derivative 3. Methylmercapt groups of 3 were readily converted to formyl groups by Vilsmeier reaction to afford 3,3′-diformyl-1,1′-biazulene (4), which reacted with pyrrole in the presence of acetic acid to give the parent 1,1′-biazulene (5). Reaction of 5 with pyridine in the presence of Tf2O gave 3,3′-dihydropyridyl-1,1′-biazulene derivative 6. 3,3′-(4-Pyridyl)-1,1′-biazulene (7) was obtained by the reaction of 3 with KOH in EtOH at room temperature in good yield. |
| Keywords: | Azulene Biazulene Aryl-aryl coupling Pyridinylation |
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