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Synthesis 2008(23): 3745-3748  
DOI: 10.1055/s-0028-1083224
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Easy Access to 2-Substituted Azulenes from Azulene-2-boronic Acid Pinacol Ester

Masayuki Fujinagaa, Kouichi Suetakeb, Kazuhiro Gyojia, Toshihiro Murafuji*a,b, Kei Kurotobib, Yoshikazu Sugihara*b
a Graduate School of Medicine, Yamaguchi University, Yamaguchi City 753-8512, Japan
b Department of Chemistry, Faculty of Science, Yamaguchi University, Yamaguchi City 753-8512, Japan
Fax: +81(83)9335738; e-Mail: murafuji@yamaguchi-u.ac.jp; e-Mail: sugihara@yamaguchi-u.ac.jp;
Further Information

Publication History

Received 26 June 2008
Publication Date:
14 November 2008 (online)

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Abstract

Azulene-2-boronic acid pinacol ester was conveniently transformed into 2-substituted azulenes bearing carboxyl, formyl, ester, or amino groups, which are difficult to access by conventional methods. Furthermore, the azulene-2-carboxylic acid thus synthesized was subjected to the Ugi four-component condensation to obtain a dipeptide-type product containing an azulene skeleton.

Key words

azulene - borylation - boronic acid ester - cross-coupling - Ugi four-component reaction

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