Synthesis of 1-(pyridyl, quinolyl, and isoquinolyl)azulenes by Reissert–Henze type reaction

✍ Scribed by Taku Shoji; Kazuyuki Okada; Shunji Ito; Kozo Toyota; Noboru Morita

• Book ID: 104098111
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 514 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.07.090

✦ Synopsis

Azulene derivatives reacted with N-oxide of several heterocycles in the presence of trifluoromethanesulfonic anhydride (Tf 2 O) to afford 1-(pyridyl, quinolyl, and isoquinolyl)azulenes in good yield, respectively. In the case of the reaction with the 1-azulenyl methyl sulfide (12), 1,1 0 -biazulene derivative 13 was obtained under the similar reaction conditions. The first synthesis of unsymmetrical 1,3-di(pyridyl)azulene derivative was also established via our new preparation method following the electrophilic pyridinylation using the reaction with pyridine in the presence of Tf 2 O.