微波促进合成苝单酰亚胺类化合物

doi:10.6023/cjoc202008010

有机化学 ›› 2021, Vol. 41 ›› Issue (2): 702-707.DOI: 10.6023/cjoc202008010 上一篇下一篇

研究论文

微波促进合成苝单酰亚胺类化合物

王雅楠¹, 王冲¹, 祁禹鸣¹, 李国凯¹, 李小六¹^,^*(), 王克让¹^,^*()

1 河北大学化学与环境科学学院药物化学与分子诊断教育部重点实验室河北省化学生物学重点实验室河北保定 071002

收稿日期:2020-08-09 修回日期:2020-09-27 发布日期:2020-10-15
通讯作者: 李小六, 王克让
作者简介:
* Corresponding authors. E-mail: kerangwang@hbu.edu.cn; lixl@hbu.edu.cn
† 共同第一作者(These authors contributed equally to this work).
基金资助:
国家自然科学基金(21572044); 国家自然科学基金(21778013); 河北省科技厅(19241303D)

Microwave-Assisted Synthesis of Perylene Monoimide Derivatives

Ya'nan Wang¹, Chong Wang¹, Yuming Qi¹, Guokai Li¹, Xiaoliu Li¹^,^*(), Kerang Wang¹^,^*()

1 Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002

Received:2020-08-09 Revised:2020-09-27 Published:2020-10-15
Contact: Xiaoliu Li, Kerang Wang
Supported by:
the National Natural Science Foundation of China(21572044); the National Natural Science Foundation of China(21778013); and the Foundation of the Department of Science and Technology of Hebei Province(19241303D)

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摘要/Abstract

以3,4;9,10-苝四甲酸酐为原料, 经微波促进反应探讨了反应底物用量、反应时间和反应温度等条件对反应收率的影响, 合成了系列苝单酰亚胺类化合物, 其中2,6-二异丙基苯胺修饰的苝单酰亚胺化合物N-2',6'-二异丙基苯胺基- 3,4-苝单酰亚胺(PMI-1)在30 min的反应时间内, 分离收率可达64.1%.

关键词: 苝单酰亚胺, 微波促进合成, 苝四甲酸酐, 有机胺

A fast and efficient method for the synthesis of aromatic amine modified perylene monoimide derivatives based on microwave-assisted reaction was developed. It is found that the amount of 2,6-diisopropylaniline showed very important influences on the synthetic yield. N-2',6'-Diisopropylanilino-3,4-perylene monoimide (PMI-1) was obtained with the isolated yield of 64.1% under the optimized condition of 7 equiv. of 2,6-diisopropylaniline at 170 ℃ and 80 W for 30 min.

Key words: perylene monoimide, microwave-assisted synthesis, perylene tertracarboxylic dianhydride, organic amine

引用此文

王雅楠, 王冲, 祁禹鸣, 李国凯, 李小六, 王克让. 微波促进合成苝单酰亚胺类化合物[J]. 有机化学, 2021, 41(2): 702-707.

Ya'nan Wang, Chong Wang, Yuming Qi, Guokai Li, Xiaoliu Li, Kerang Wang. Microwave-Assisted Synthesis of Perylene Monoimide Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 702-707.

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图/表 7

图式1. 苝单酰亚胺化合物PMI-1的合成路线

Scheme 1. Synthesis route of perylene monoimide derivatives PMI-1

Entry	Time/min	Temp./℃	Yield^a/%
1	20	170	15.2
2	30	170	18.0
3	40	170	15.7
4	50	170	21.9
5	60	170	24.5
6	30	160	16.3
7	30	170	18.0
8	30	180	14.7

表1. 不同时间和温度对合成PMI-1的影响

Table 1. Effect of different time and temperature on the synthesis of compound PMI-1

Entry	V(H₂O)/ mL	m(imidazole)/ g	m(Zn(OAc)₂?H₂O)/ g (equiv.)	Yield^a/%
1	2	10.2	1.40 (3)	17.6
2	3	10.2	1.40 (3)	18.0
3	4	10.2	1.40 (3)	17.1
4	3	5.1	1.40 (3)	16.5
5	3	10.2	1.40 (3)	18.0
6	3	10.2	0.467 (1)	15.5
7	3	10.2	0.935 (2)	16.9
8	3	10.2	1.40 (3)	18.0
9	3	10.2	1.868 (4)	15.3

表2. H2O、咪唑和Zn(OAc)2?H2O的用量对合成PMI-1的影响

Table 2. Effect of the amount of H2O, imidazole and Zn(OAc)2? H2O on the synthesis of compound PMI-1

Entry	2,6-diisopropylaniline (mL/equiv.)	Yield^a/%
1	0.24/0.5	13.0
2	0.48/1	18.0
3	0.72/1.5	25.7
4	0.96/2	34.6
5	1.20/2.5	35.3
6	1.44/3	36.0
7	1.92/4	37.9
8	2.4/5	41.2
9	2.88/6	46.4
10	3.36/7	64.1
11	3.84/8	56.3
12	4.8/10	53.1

表3. 2,6-二异丙基苯胺的用量对PMI-1收率的影响

Table 3. Equivalent effects of 2,6-diisopropylaniline of synthesis of compound PMI-1

图式2. 化合物PMI-2~PMI-10的合成

Scheme 2. Synthesis of compounds PMI-2~PMI-10

图1. PBI-6An、PBI-12An、PBI-14An和PBI-18An的结构

Figure 1. Structures of PBI-6An, PBI-12An, PBI-14An and PBI-18An

Content	Yield^a/% with 1 equiv. amine	Yield^a/% with 7 equiv. amine
PMI-2	10.8	23.4
PMI-3	35.3	46.9
PMI-4	34.2	11.0
PMI-5	17.0	32.0
PMI-6	26.6	0
PMI-7	12.0	0.96
PMI-8	12.5	0
PMI-9	8.1	0
PMI-10	0	2.0

表4. 不同芳香胺和脂肪胺修饰苝单酰亚胺类化合物合成的收率

Table 4. Yields of a series of perylene monoimide derivatives with aromatic amines and fatty amines conjugates

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微波促进合成苝单酰亚胺类化合物

Microwave-Assisted Synthesis of Perylene Monoimide Derivatives

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