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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 4
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Original Articles

REACTION OF 1-(ETHOXYCARBONYLACETYL)- CYCLOHEPTA-1,3,5-TRIENE WITH ACETIC ANHYDRIDE: A FACILE SYNTHESIS OF 1-ACETOXY- 2-ACETYLAZULENES

Takanori Kajioka Toyota Central R&D Labs., Nagakute, Aichi, 480-1192, Japan
,
Mitsunori Oda Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama, 930-8555, Japan
,
Ritsu Senkuro Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama, 930-8555, Japan
&
Shigeyasu Kuroda Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama, 930-8555, Japan
Pages 627-636 | Received 11 Jan 2001, Published online: 16 Aug 2006
 
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ABSTRACT

Reaction of 1-(ethoxycarbonylacetyl)cyclohepta-1,3,5-triene (1) with acetic anhydride in the presence of sodium acetate gave 1,3-diacetoxy-2-acetylazulene (2) in 26% yield. On the other hand, a similar reaction in the presence of sodium acetate and aluminium chloride provided 1-acetoxy-2-acetyl-3-methylazulene (5) as a major product in 19% yield, accompanied with a 9% yield of 2.

ACKNOWLEDGMENT

This work was supported by a Grant-in-Aid for Scientific Research (No. 10640513 to S. K.) from the Ministry of Education, Science, Culture, and Sports, Japan. We thank Dr. Ryuta Miyatake for helpful discussion and also Ms. Kanae Haramoto for their technical assistance.

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