Palladium-Catalyzed Efficient Synthesis of 1,3-Diformylazulene Derivatives

Journal of Petrochemical Universities ›› 2010, Vol. 23 ›› Issue (2): 64-66.

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Palladium-Catalyzed Efficient Synthesis of 1,3-Diformylazulene Derivatives

Liaoning Key Laboratory of Synthesis and Application of Functional Compound, Bohai University, Jinzhou Liaoning 121003,P.R.China

Received:2009-12-15 Published:2010-06-25 Online:2010-06-25

钯催化下1,3-二甲酰基薁类衍生物的合成

邢锦娟,王道林,林立男,钱建华,刘琳

渤海大学辽宁省功能化合物合成与应用重点实验室, 辽宁锦州121003

作者简介:邢锦娟(1980 -), 女, 山西原平市
基金资助:
辽宁省教育厅创新团队资助项目(2008T001);辽宁省优秀人才支持计划资助项目(2009R02)

Abstract

Abstract:

1,3-diformylazulene was synthesized by 1,3-dibromoazulenes, organic base and catalyst under 6×10⁶ Pa at 120 ℃ with carbon monoxide-hydrogen for the formylation reagent, while palladium(Ⅱ) was as the catalyst，benzene as solvent. The yield was 77% under the condition the molar ratio of 1,3-dibromoazulenes,organic base and catalyst was 1∶2∶0.02. Based on the reaction, by changing the substituent, 1,3 - dimethylacyl-5-methyl azulene, 1,3-dimethylacyl-6-tert-butyl-azulene, 1,3-diformy-2,4,6-trimethyl-azulene were synthesized by acylation reactions, the yields were 68%, 60%, 65%. This method provides several advantages such as good yields, simple work-up procedures and mild conditions. All the products are confirmed by 1H-NMR, IR spectra and elemental analysis.

Key words:

Azulene, , 1,3-Diformylazulene, , Carbon monoxide-hydrogen, , Palladium catalyst, , Synthesis

摘要： 在钯催化作用下, 以一氧化碳和氢气为甲酰化试剂, 以苯做反应溶剂, 在6 ×106 Pa、120 ℃下, 反应底
物、有机碱和催化剂的物质的量比为1 ∶2∶0 .02 , 合成了1, 3 -二甲酰基薁, 产品收率为77 %。在此反应条件基础
上, 通过改变取代基, 进行酰基化反应合成了1, 3-二甲酰基-5 -甲基薁, 1 , 3 -二甲酰基-6-叔丁基薁, 1 , 3 -二
甲酰基-2 , 4 , 6 -3 甲基薁3 种薁类衍生物, 收率分别为68%、60 %、65 %。实验反应收率良好、操作简单、条件温和。
4 种新型化合物的产品结构通过红外光谱仪、核磁共振光谱仪以及元素分析仪进行了表征。

关键词: 薁 , 1, 3 -二甲酰基薁 , 一氧化碳-氢气 , 钯催化 , 合成

XING Jin-juan, WANG Dao-lin, LIN Li-nan, et al. Palladium-Catalyzed Efficient Synthesis of 1,3-Diformylazulene Derivatives[J]. Journal of Petrochemical Universities, 2010, 23(2): 64-66.

邢锦娟,王道林,林立男. 钯催化下1,3-二甲酰基薁类衍生物的合成[J]. 石油化工高等学校学报, 2010, 23(2): 64-66.

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Palladium-Catalyzed Efficient Synthesis of 1,3-Diformylazulene Derivatives

钯催化下1,3-二甲酰基薁类衍生物的合成

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