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    Title: Diazotization of Methyl 3-Amino-7-isopropyl-2- methoxyazulene-1-carboxylate and Its 5-Isopropyl Isomer---A Convenient Synthesis of 1,2-Azulenequinone Derivatives
    Authors: Huang, Tian-chyuan;Lin, Yun-shan;Lin, Shih-jue;Chu, Shu-fan
    Contributors: 淡江大學化學學系
    Keywords: Diazotization;Azulenequinone;Azulene;Synthesis;重氮化;薁醌;;合成
    Date: 1996-02
    Issue Date: 2013-07-29 13:48:37 (UTC+8)
    Publisher: 臺北市:中國化學學會
    Abstract: Methyl 3-amino-2-methoxy-7-isopropylazulene-1- carboxylate (8a) and its 5-isopropyl isomer (8b) were synthesized by reduction of the 3-nitro derivatives (7a,b) with zinc/acetic acid in excellent yields. 7a and 7b were prepared by nitration and methylation of methyl 7-isopropyl- 2-hydroxyazulene-1-carboxylate and methyl 5-isopropyl-2- hydroxyazulene-1-carboxylate, respectively. Diazotization of 8a with sodium nitrite in trifluoroacetic acid at 0.degree.C gave methyl 5-isopropyl-1,2- azulenequinone-3- carboxylate 9a in 91% yield. Similar reaction of 8b gave the corresponding methyl 7-isopropyl-1,2-azulenequinone-3- carboxylate 9b in 93% yield. No evidence for the formation of 1-diazo-1,2-azulenequinones was obtained.
    Relation: Journal of the Chinese Chemical Society=中國化學會會誌 43(1), pp.41-44
    DOI: 10.1002/jccs.199600007
    Appears in Collections:[化學學系暨研究所] 期刊論文

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