Diazotization of Methyl 3‐Amino‐7‐Isopropyl‐2‐Methoxyazulene‐1‐Carboxylate and its 5‐Isopropyl Isomer‐ a Convenient Synthesis of 1,2‐Azulenequinone Derivatives
作者:
Tian‐Chyuan Huang,
Yun‐Shan Lin,
Shih‐Jue Lin,
Shu‐Fan Chu,
期刊:
Journal of the Chinese Chemical Society
(WILEY Available online 1996)
卷期:
Volume 43,
issue 1
页码: 41-44
ISSN:0009-4536
年代: 1996
DOI:10.1002/jccs.199600007
出版商: WILEY‐VCH Verlag
关键词: 3‐Amino‐2‐methoxyazulene;Diazotization;Azulenyl‐1‐diazonium salt;l‐Diazo‐1,2‐azulenequinone;1,2‐Azulenequinone
数据来源: WILEY
摘要:
AbstractMethyl 3‐amino‐2‐methoxy‐7‐isopropylazulene‐l‐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.7aand7bwere prepared by nitration and methylation of methyl 7‐isopropyl‐2‐hydroxyazulene‐l‐carboxylate (5a) and methyl 5‐isopropyl‐2‐hydroxyazulene‐l‐carboxylate (5b), respectively. Diazotization of8awith sodium nitrite in trifluoroacetic acid at 0 °C gave methyl 5‐isopropyl‐1,2‐azulenequinone‐3‐carboxylate (9a) in 91% yield. Similar reaction of8bgave the corresponding methyl 7‐isopropyl‐1,2‐azulenequinone‐3‐carboxylate (9b) in 93% yield. No evidence for
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