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A simple and efficient synthesis of 2-alkylazulenes
Authors:Naoshi Iwama  Masami Kashimoto  Taku Kato  Toshihiko Sugano
Institution:a Polymerization Technical Center, Japan Polypropylene Corp., Yokkaichi, Mie 510-0848, Japan
b Organic Synthesis and Molecular Catalysis Laboratory, Mitsubishi Chemical Group Science and Technology Research Center, Inc., Aoba-ku, Yokohama 227-8502, Japan
c Research and Development Division, Japan Polychem Corp., Yokkaichi, Mie 510-0848, Japan
Abstract:The annulation method based on 2H-cycloheptab]furan-2-ones was applied for the synthesis of 2-alkylazulenes; 2-R-azulene (R = Et, i-Pr, n-Pr, i-Bu). Tropolone p-toluenesulfonate was used as a starting compound. By the two step synthesis, 1-carboxylic-3-cyanoazulene derivatives were obtained. Treatment of 1-carboxylic-3-cyanoazulene derivatives with aq H2SO4 resulted in decarboxylation and elimination of cyano group to give 2-alkylazulenes in good yields.
Keywords:Azulene  Alkylazulene  Tropolone
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