Heteroarylation of 1‐Azulenyl Methyl Sulfide: Two‐Step Synthetic Strategy for 1‐Methylthio‐3‐(heteroaryl)azulenes Using the Triflate of N‐Containing Heterocycles

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 t...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-12, Vol.2008 (34), p.5823-5831
Main Authors: Higashi, Junya, Shoji, Taku, Ito, Shunji, Toyota, Kozo, Yasunami, Masafumi, Morita, Noboru
Format: Article
Language:English
Subjects:
Azulene
Electrochemistry
Electrophilic Substitution
Heteroarylation
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Summary: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 tBuOK 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) 1‐Azulenyl methyl sulfide reacts with highly electrophilic trifluoromethanesulfonates of N‐heterocycles to give 1‐methylthio‐3‐(dihydroheteroaryl)azulenes in good yields. Treatment of these azuleneswith KOH or tBuOK afforded 1‐methylthio‐3‐(heteroaryl)azulenes in good yields. The redox behavior of the 1‐methylthio‐3‐(heteroaryl)azulenes was examined by cyclic voltammetry.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200800733