Diazotization of Methyl 3-Amino-7-isopropyl-2- methoxyazulene-1-carboxylate and Its 5-Isopropyl Isomer---A Convenient Synthesis of 1,2-Azulenequinone Derivatives

淡江大學機構典藏 > 理學院 > 化學學系暨研究所 > 期刊論文 > Item 987654321/4427

Citation Infomation

Please use this identifier to cite or link to this item: https://tkuir.lib.tku.edu.tw/dspace/handle/987654321/4427

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;薁;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

Files in This Item:

File	Size	Format
0009-4536_43(1)p41-44.pdf	136Kb	Adobe PDF	232	View/Open