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    Title: Synthesis and Diazotization of Diethyl 6-Amino-2- hydroxyazulene-1,3-dicarboxylate and Its 2-Acetoxyl Derivative
    Authors: Hunag, Tian-chyuan;Morita, Tadayoshi;Lin, Bing-bing;Lin, Yun-shan
    Contributors: 淡江大學化學學系
    Keywords: 6-Azideazulene;Diazotization;Synthesis;Azulenyl Diazonium Salt;疊氮薁;重氮化;合成;薁基重氮離子鹽
    Date: 1994-04
    Issue Date: 2013-07-29 13:38:56 (UTC+8)
    Publisher: 臺北市:中國化學學會
    Abstract: Diethyl 6-amino-2-hydroxyazulene-1,3-dicarboxylate(6a) and 2-acetoxyl derivative (6b) were synthesized by reduction of the 6-azido derivatives (5a,b) with zinc/acetic acid in excellent yields. (5a) and (5b) were prepared by azidation of diethyl 2- acetoxy-6-bromoazulene- 1,3-dicarboxylate. Diazotization of (6a) with sodium nitrite in the presence of concentrated sulfuric acid in dioxane gave diethyl 2-hydroxy-, 2,6-dihydroxy-, and 2- hydroxy-6- [ 2-(2-hydroxyethoxy)ethoxy ] -azulene-1,3- dicarboxylates in 5, 35 and 20% yields, respectively. Similar reaction of (6b) gave the corresponding acetates, compounds of the same type from (6a). No evidence for the formation of 6-diazo-1,3-diethoxycarbonyl-2(6H) azulenone was obtained in the employed reaction conditions.
    Relation: Journal of the Chinese Chemical Society=中國化學會會誌 41(2), pp.199-203
    DOI: 10.1002/jccs.199400029
    Appears in Collections:[化學學系暨研究所] 期刊論文

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