基于Ugi四组分反应合成结构多样的新型分散染料

doi:10.6023/cjoc202010033

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1703-1711.DOI: 10.6023/cjoc202010033 上一篇下一篇

研究论文

基于Ugi四组分反应合成结构多样的新型分散染料

郭小燕^a, 方帅军^b, 钱红飞^b, 冯高峰^a^,^*()

a 绍兴文理学院浙江省精细化学品传统工艺替代技术研究重点实验室浙江绍兴 312000
b 绍兴文理学院纺织服装学院浙江绍兴 312000

收稿日期:2020-10-22 修回日期:2020-11-13 发布日期:2020-12-05
通讯作者: 冯高峰
基金资助:
国家自然科学基金(21676166)

Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction

Xiaoyan Guo^a, Shuaijun Fang^b, Hongfei Qian^b, Gaofeng Feng^a^,^*()

a Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang 312000
b College of Textile and Garment, Shaoxing University, Shaoxing, Zhejiang 312000

Received:2020-10-22 Revised:2020-11-13 Published:2020-12-05
Contact: Gaofeng Feng
About author:
* Corresponding author. E-mail: chfeng@usx.edu.cn
Supported by:
National Natural Science Foundation of China(21676166)

文章分享

1. cjoc202010033辅助材料.pdf(3310KB)

摘要/Abstract

以Ugi四组分反应为关键步骤, 建立了一种合成结构多样、色牢度性能优异新型分散染料的新方法. 从简单易得的原料出发, 经过4-氧代丁酸衍生物合成, 酸、苯胺、苯甲醛和环己基异氰的Ugi四组分反应以及Ugi产物与重氮盐偶合等步骤合成了15个新颖的分散染料. 用¹H NMR、¹³C NMR、红外光谱、质谱和高分辨质谱对Ugi产物和新染料的结构进行了表征, 并测试了他们的可见光吸收和摩尔消光系数. 在聚酰胺和聚酯纤维上色牢度的研究发现, 新型分散染料的色牢度比已知分散染料红1和红13有了很大提高. 色牢度的提高与分散染料中引入的两个酰胺基和一个酯基以及染料分子量/体积的适当提高相关. 这是一个合成新型高性能分散染料分子库的有效方法.

关键词: 分散染料, Ugi四组分反应, 多样性导向合成, 色牢度, 氢键作用

A novel approach has been established for synthesizing novel structurally diverse azo disperse dyes with good fastness properties by employing Ugi four-component reaction as the key step. 15 new disperse azo dyes were synthesized efficiently from readily available starting materials with simple operations through a sequence of generation of 4-(2-(ethyl (phenyl)amino)ethoxy)-4-oxobutanoic acid, the Ugi four-component reactions of the acid with anilines, benzaldehydes and cyclohexyl isocyanide, and the coupling of the Ugi adducts with aryl diazonium salts. The structures of Ugi adducts and the new dyes were fully characterized with ¹H NMR, ¹³C NMR, IR, MS, and HRMS. Visible absorption measurements and molar extinction coefficients were also carried out. It was found that the obtained dyes exhibited improved fastness properties on both polyamide (PA) and poly(ethylene terephthalate) (PET) fabrics as compared with C. I. Disperse Red 1 and C. I. Disperse Red 13. The improvement of fastness properties should be attributed to the introduced two amides and one ester functionalities, and the appropriately increased molecular weight/size. It is an attractive approach for accessing a library of novel azo disperse dyes with good fastness properties.

Key words: azo disperse dye, Ugi four-component reaction, diversity-oriented synthesis, fastness property, hydrogen-bonding interaction

引用此文

郭小燕, 方帅军, 钱红飞, 冯高峰. 基于Ugi四组分反应合成结构多样的新型分散染料[J]. 有机化学, 2021, 41(4): 1703-1711.

Xiaoyan Guo, Shuaijun Fang, Hongfei Qian, Gaofeng Feng. Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1703-1711.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 5

参考文献 12

[1]	(a) Gharanjig, K.; Arami, M.; Bahrami, H.; Movassagh, B.; Mohamoodi, N.M.; Rouhani, S. Dyes Pigm. 2008, 76,684.
	Wang, J.-X.; Zhang, S.-F.; Tang, B.-T.; Yang, J.-Z.; Zhao, D. Dyest. Color. 2006, 43,5. (in Chinese)
	( 王杰雄, 张淑芬, 唐炳涛, 杨锦宗, 赵丹, 染料与染色, 2006, 43,5.)
[2]	(a) Rizk, H.F.; Ei-Borai, M.A.; Ei-hefnawy, G.B.; Ei-sayed, H.F. Chin. J. Chem. 2009, 27,1359.
	(b) Yazdanbakhsh, M.R.; Mohammadi, A.; Mohajerani, E.; Nemati, H.; Nataj, N.H.; Moheghi, A.; Naeemikhah, E. J. Mol. Liq. 2010, 151,107.
	(c) Deshmukh, M.S.; Sekar, N.A. Dyes Pigm. 2014, 103,25.
[3]	(a) Satam, M.A.; Raut, R.K.; Sekar, N. Dyes Pigm. 2013, 96,92.
	(b) Qiu, J.; Tang, B.; Ju, B.; Zhang, S.; Jin, X. Dyes Pigm. 2020, 173,107920.
[4]	(a) Ameuru, U.S.; Yakubu, M.K.; Bello, K.A.; Nkeonye, P.O.; Halimehjani, A.Z. Dyes Pigm. 2018, 157,190.
	(b) Fang, S.; Feng, G.; Guo, Y.; Chen, W.; Qian, H. Dyes Pigm. 2020, 176,108225.
	(c) Demirçalı, A.; Karcı, F.; Avinc, O.; Kahrıman, A.U.; Gedik, G.; Bakan, E. J. Mol. Struct. 2019, 1181,8.
[5]	(a) Qiu, J.; Xiao, J.; Tang, B.; Ju, B.; Zhang, S. Dyes Pigm. 2019, 160,524.
	(b) Cui, Z.; Cheng, X.; Li, X.; Lu, H.H.; Wang, X.D.; Chen, W.G. Chin. Chem. Lett. 2014, 25,1121.
[6]	(a) Nazeri, M.T.; Farhid, H.; Mohammadian, R.; Shaabani, A. J. Org. Chem. 2018, 83,12921. pmid: 33052681
	(b) Shaabani, S.; Dömling, A. Angew Chem., Int. Ed. 2018, 57,16266. pmid: 33052681
	(c) Feng, Q.Y.; Zhu, J.; Wang, M.-X.; Tong, S. Org. Lett. 2020, 22,483. pmid: 33052681
	(d) Pertejo, P.; González-Saiz, B.; Quesada, R.; García-Valverde, M. J. Org. Chem. 2020, 85,14240. pmid: 33052681
[7]	Li, X.; Jia, X.; Yin, L. Chin. J. Org. Chem. 2007, 37,2237. (in Chinese)
	( 李修明, 贾学顺, 殷亮, 有机化学, 2017, 37,2237.)
[8]	Madhavachary, R.; Zarganes-Tzitzikas, T.; Patil, P.; Kurpiewska, K.; Kalinowska-Tłuścik, J.; Dömling, A. ACS Comb. Sci. 2018, 20,192.
[9]	Hoffer, L.; Voitovich, Y.V.; Raux, B.; Carrasco, K.; Muller, C.; Fedorov, A.Y.; Derviaux, C.; Amouric, A.; Betzi, S.; Horvath, D.; Varnek, A.; Collette, Y.; Combes, S.; Roche, P.; Morelli, X. J. Med. Chem. 2018, 61,5719.
[10]	(a) Sehlinger, A.; Verbraeken, B.; Meier, M.; Hoogenboom, R.A. R. Polym. Chem. 2015, 6,3828.
	(b) Kakuchi, R. Angew. Chem., Int. Ed. 2014, 53,46.
[11]	Rocha, R.O.; Rodrigues, M.O.; Neto, B.A. D. ACS Omega 2020, 5,972.
[12]	Li, H.; Qian, H.-F.; Feng, G. Dye Pigm. 2019, 165,415.

Dye	λ_max/nm	Δν_1/2^a/nm	ε/(L?mol^–1?cm^–1)
C. I. Disperse Red 1	502	113	35995
C. I. Disperse Red 13	522	124	34118
3aa	489	112	32742
3ab	509	124	28178
3ac	436	128	24983
3ba	483	119	40043
3bb	507	132	34483
3bc	436	125	26115
3ca	486	114	27067
3cb	508	126	26042
3cc	440	124	23121
3da	487	117	36157
3db	509	134	33758
3dc	439	124	25128
3ea	490	119	40267
3eb	510	124	38953
3ec	442	128	30263

Dye	λ_max/nm	Δν_1/2^a/nm	ε/(L?mol^–1?cm^–1)
C. I. Disperse Red 1	502	113	35995
C. I. Disperse Red 13	522	124	34118
3aa	489	112	32742
3ab	509	124	28178
3ac	436	128	24983
3ba	483	119	40043
3bb	507	132	34483
3bc	436	125	26115
3ca	486	114	27067
3cb	508	126	26042
3cc	440	124	23121
3da	487	117	36157
3db	509	134	33758
3dc	439	124	25128
3ea	490	119	40267
3eb	510	124	38953
3ec	442	128	30263

Dye	Washing							Sublimation		Light	Rubbing
	Change	Staining^a						Change	Staining	Change	Dry	Wet
	Change	D	C	N	PET	PAN	W	Change	Staining	Change	Dry	Wet
C. I. Disperse Red 1	2	1	2~3	1	3	4	1~2	3~4	2	3	5	4~5
C. I. Disperse Red 13	2	1	2~3	1	3	4	2	4	2~3	2~3	5	4~5
3aa	3	5	5	4~5	5	5	5	3	5	4	4~5	4~5
3ab	4	4~5	4~5	4	4~5	5	4~5	3~4	5	3~4	4~5	4
3ac	4	4~5	4~5	4~5	4~5	5	4~5	4~5	4~5	4	4~5	4
3ba	4~5	5	4~5	4~5	5	5	4~5	4~5	4~5	4	5	5
3bb	4~5	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3bc	4	4~5	4~5	4	4~5	5	4~5	4~5	4~5	4	3~4	4~5
3ca	4~5	3	4~5	3	4~5	4~5	4~5	4~5	4	4	4~5	3~4
3cb	4	3~4	4~5	3	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3cc	3~4	3~4	4~5	3~4	4~5	4~5	4~5	4~5	4~5	4	3	2~3
3da	4	4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4	4~5
3db	4~5	4~5	4	4~5	4~5	5	5	4	5	3~4	5	4
3dc	2~3	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3ea	2~3	2~3	4~5	2	4~5	5	4	4	3~4	3~4	5	5
3eb	3	3	4~5	2~3	4~5	5	4~5	4	4~5	2~3	4~5	4~5
3ec	3	3	4~5	3	4~5	4-5	4~5	4	4~5	4~5	4~5	5

Dye	Washing							Sublimation		Light	Rubbing
	Change	Staining^a						Change	Staining	Change	Dry	Wet
	Change	D	C	N	PET	PAN	W	Change	Staining	Change	Dry	Wet
C. I. Disperse Red 1	2	1	2~3	1	3	4	1~2	3~4	2	3	5	4~5
C. I. Disperse Red 13	2	1	2~3	1	3	4	2	4	2~3	2~3	5	4~5
3aa	3	5	5	4~5	5	5	5	3	5	4	4~5	4~5
3ab	4	4~5	4~5	4	4~5	5	4~5	3~4	5	3~4	4~5	4
3ac	4	4~5	4~5	4~5	4~5	5	4~5	4~5	4~5	4	4~5	4
3ba	4~5	5	4~5	4~5	5	5	4~5	4~5	4~5	4	5	5
3bb	4~5	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3bc	4	4~5	4~5	4	4~5	5	4~5	4~5	4~5	4	3~4	4~5
3ca	4~5	3	4~5	3	4~5	4~5	4~5	4~5	4	4	4~5	3~4
3cb	4	3~4	4~5	3	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3cc	3~4	3~4	4~5	3~4	4~5	4~5	4~5	4~5	4~5	4	3	2~3
3da	4	4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4	4~5
3db	4~5	4~5	4	4~5	4~5	5	5	4	5	3~4	5	4
3dc	2~3	3~4	4~5	3~4	4~5	5	4~5	4~5	4~5	3~4	4~5	4~5
3ea	2~3	2~3	4~5	2	4~5	5	4	4	3~4	3~4	5	5
3eb	3	3	4~5	2~3	4~5	5	4~5	4	4~5	2~3	4~5	4~5
3ec	3	3	4~5	3	4~5	4-5	4~5	4	4~5	4~5	4~5	5

Dye	Washing							Sublimation		Light	Rubbing
	Change	Staining^a						Change	Staining	Change	Dry	Wet
	Change	D	C	N	PET	PAN	W	Change	Staining	Change	Dry	Wet
C. I. Disperse Red 1	4~5	4~5	5	4~5	5	5	5	3~4	2	4	5	5
C. I. Disperse Red 13	4	5	5	4~5	5	5	5	4	2~3	4	4~5	5
3aa	4	5	5	5	5	5	5	4	5	4~5	4~5	5
3ab	4~5	4~5	4~5	5	5	5	5	3~4	5	6	4~5	5
3ac	5	5	5	5	5	5	5	4~5	5	7	4~5	5
3ba	5	5	4~5	5	5	5	5	4~5	5	4	5	5
3bb	5	5	4~5	5	5	5	5	5	5	6	5	5
3bc	4~5	5	5	5	5	5	5	4~5	4~5	6	5	5
3ca	4~5	5	5	5	5	5	5	4~5	4~5	4~5	4~5	5
3cb	4	5	5	4~5	5	5	5	5	4~5	6	3~4	4~5
3cc	4~5	5	5	5	5	5	5	4~5	5	7	5	5
3da	5	5	4~5	5	5	5	5	4~5	4~5	4	5	5
3db	4~5	5	5	5	5	5	5	3~4	5	4~5	3~4	4~5
3dc	5	5	5	5	5	5	5	5	4~5	6	5	5
3ea	5	4~5	5	4~5	5	5	5	4~5	4	4	4~5	5
3eb	4~5	4~5	5	4~5	5	5	5	4~5	4~5	4~5	4~5	4~5
3ec	4	4~5	4~5	4~5	5	5	5	3~4	4~5	4	4~5	5

基于Ugi四组分反应合成结构多样的新型分散染料

Facile Synthesis of Novel, Structurally Diverse Azo Disperse Dyes by Employing Ugi Four-Component Reaction

RichHTML

PDF

补充材料

可视化

摘要/Abstract

引用此文

分享此文

图/表 5

参考文献 12

相关文章 7

编辑推荐

相关统计

本文评价

[1]	罗享豪, 谢益碧, 黄年玉, 王龙. 基于原位捕获异腈的Ugi四组分反应及其后修饰串联反应: 一锅法合成含氮杂环化合物[J]. 有机化学, 2022, 42(3): 838-846.
[2]	刘金妮, 谢益碧, 阳青青, 黄年玉, 王龙. 基于原位捕获胺的Ugi四组分反应及其后修饰串联环化反应:“一锅法”合成六元、七元杂环化合物[J]. 有机化学, 2021, 41(6): 2374-2383.
[3]	赵宇, 刘鑫磊, 李益豪, 许磊川, 苏彦豪, 蒋家珍, 王明安. (E)-3-(1-亚胺基乙基)-5,5-二取代-4-甲氨基呋喃-2(5H)-酮的合成及其意外的杀虫活性[J]. 有机化学, 2020, 40(8): 2547-2554.
[4]	关爱莹, 赵宇, 王卫伟, 刘鑫磊, 王明安. 3-乙酰基-4-苯基-1-氧代螺[4,5]癸-3-烯-2-酮类衍生物的合成及杀菌活性[J]. 有机化学, 2018, 38(10): 2767-2774.
[5]	颜廷斌, 刘跃辉, 沈悦海. 钌催化烯烃复分解反应中的氢键效应[J]. 有机化学, 2018, 38(10): 2491-2500.
[6]	黄志斌, 刘学成, 胡明华, 林伟, 史达清. 吡啶并[2,3-d]嘧啶衍生物受体的合成及对阴离子识别研究[J]. 有机化学, 2014, 34(2): 382-386.
[7]	王云明, 唐炳涛, 马威, 张淑芬. 紫外吸收染料研究进展[J]. 有机化学, 2010, 30(03): 330-337.