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Synthesis 1999; 1999(1): 184-187
DOI: 10.1055/s-1999-3678
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An Efficient Synthetic Pathway from Cyclohepta-1,3,5-triene to 2,3-Disubstituted 1,2,3,8-Tetrahydroazulen-1-ones

Takanori Kajioka* , Mitsunori Oda, Shin'ichiro Yamada, Yoshio Kawamori, Ryuta Miyatake, Shigeyasu Kuroda
  • *Department of Applied Chemistry, Faculty of Engineering, Toyama University, Gofuku 3190, Toyama 930-8555, Japan; Fax +81(7 64)45 68 19; E-mail: oda@eng.toyama.u.ac.jp
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Publication Date:
31 December 1999 (online)

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The Nazarov cyclization of substituted ethyl 3-(cyclohepta-1,3,5-trien-1-yl)-2-methylen-3-oxopropionates, prepared from cyclohepta-1,3,5-triene in three steps, gave solely 2,3-disubstituted 1,2,3,8-tetrahydroazulen-1-ones without any detectable formation of its double bond regioisomer.

Nazarov reaction - electrocyclization - azulenones - trimethylsilyl triflate