A simple and efficient synthesis of 2-alkylazulenes |
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Authors: | Naoshi Iwama Masami Kashimoto Taku Kato Toshihiko Sugano |
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Affiliation: | 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 |
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Abstract: | The annulation method based on 2H-cyclohepta[b]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. |
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Keywords: | Azulene Alkylazulene Tropolone |
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