Diazotization of methyl 3-amino-7-isopropyl-2-methoxyazulene-1-carboxylate and its 5-isopropyl isomer - A convenient synthesis of 1,2-azulenequinone derivatives

被引：1

作者：

Huang, TC ^{[1
]}

Lin, YS ^{[1
]}

Lin, SJ ^{[1
]}

Chu, SF ^{[1
]}

机构：

[1] TAMKANG UNIV,DEPT CHEM,TAIPEI 25137,TAIWAN

来源：

JOURNAL OF THE CHINESE CHEMICAL SOCIETY | 1996年 / 43卷 / 01期

关键词：

3-amino-2-methoxyazulene; diazotization; azulenyl-1-diazonium salt; 1-diazo-1,2-azulenequinone; 1,2-azulenequinone;

D O I：

10.1002/jccs.199600007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 (5a) and methyl 5-isopropyl-2-hydroxyazulene-1-carboxylate (5b), respectively. Diazotization of 8a with sodium nitrite in trifluoroacetic acid at 0 degrees 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.

引用

页码：41 / 44

页数：4

共 10 条

[1]

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[2]

MACDONALD RN, 1976, J CHEM SOC CHEM COMM, P605

[3] SYNTHESIS AND SOME PROPERTIES OF 1,2-AZULENEQUINONE (1,2-AZULENEDIONE) AND ITS DERIVATIVES [J].