Microwave-Assisted Synthesis of Perylene Monoimide Derivatives

doi:10.6023/cjoc202008010

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 702-707.DOI: 10.6023/cjoc202008010 Previous Articles Next Articles

Article

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)

1. cjoc202008010.pdf(1103KB)

Abstract

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

Cite this article

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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Fig. & Tab. 7

References 20

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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

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

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

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

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

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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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

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