Heteroarylation of 1-Azulenyl Methyl Sulfide: Two-Step Synthetic Strategy for 1-Methylthio-3-(heteroaryl)azulenes Using the Triflate of N-Containing Heterocycles
✍ Scribed by Junya Higashi; Taku Shoji; Shunji Ito; Kozo Toyota; Masafumi Yasunami; Noboru Morita
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 290 KB
- Volume
- 2008
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
1‐Azulenyl methyl sulfide reacts with highly electrophilic trifluoromethanesulfonates of N‐heterocycles, that is, pyridine, isoquinoline, 1,10‐phenanthroline, benzothiazole, quinoline, and acridine, to give 1‐methylthio‐3‐(dihydroheteroaryl)azulenes in good yields. In the case of the reaction with the trifluoromethanesulfonate of pyridine, 1‐methylthio‐3‐pyridylazulene was obtained directly under certain reaction conditions. Treatment of the 1‐methylthio‐3‐(dihydroheteroaryl)azulenes with KOH or __t__BuOK afforded the corresponding 1‐methylthio‐3‐(heteroaryl)azulenes in good yields. The redox behavior of these 1‐methylthio‐3‐(heteroaryl)azulenes was examined by cyclic voltammetry and differential pulse voltammetry.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)