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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 16
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Original Articles

Lewis Acid-Catalyzed Cyclotrimerization of Methyl 3-Acetylazulene-1-carboxylate in Alcohols

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Pages 2757-2762 | Received 15 Oct 2002, Published online: 19 Aug 2006
 

Abstract

An alcoholic solution of methyl 3-acetylazulene-1-carboxylate was treated with tetrachlorosilane, titanium(IV) chloride, thionyl chloride, and so on, at room temperature to give 1,3,5-tri(1-azulenyl)benzenes. It was found that thionyl chloride is useful for triple condensation. A dimeric intermediate, 1,3-bis(3-methoxycarbonyl-1-azulenyl)-2-buten-1-one, was also isolated. Its reaction with the starting monomer gave the trimeric 1,3,5-tri(1-azulenyl)benzene.

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