Mechanochemical Synthesis of (2-Hydroxyphenyl)(3- quinolinyl)ketone

doi:10.6023/cjoc202411009

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2416-2424.DOI: 10.6023/cjoc202411009 Previous Articles Next Articles

ARTICLES

机械化学合成(2-羟基苯基)(3-喹啉基)甲酮

许秋玲, 孙瑞芬, 王均亮^*(), 何晓山^*()

云南中医药大学科研实验中心昆明 650500

收稿日期:2024-12-22 修回日期:2025-02-19 发布日期:2025-03-07
通讯作者: 王均亮, 何晓山
基金资助:
云南省科技厅中医药应用基础研究联合专项基金(202301AZ070001-021)

Mechanochemical Synthesis of (2-Hydroxyphenyl)(3- quinolinyl)ketone

Qiuling Xu, Ruifen Sun, Junliang Wang^*(), Xiaoshan He^*()

Yunnan University of Chinese Medicine, Center for Scientific Research, Kunming 650500

Received:2024-12-22 Revised:2025-02-19 Published:2025-03-07
Contact: Junliang Wang, Xiaoshan He
Supported by:
Yunnan Provincial Science and Technology Department-Applied Basic Research Joint Special Funds of Chinese Medicine(202301AZ070001-021)

1. .pdf(4777KB)

Abstract

A mechanochemical synthesis method was reported for the efficient preparation of (2-hydroxyphenyl) (3-quino- linyl) ketone compounds using ortho aminobenzaldehyde compounds and chromone-3-carboxaldehyde compounds for the first time. Meanwhile, it demonstrates that chemical transformations that are difficult to occur under solvent conditions can be synthesized using mechanochemical methods to produce the target product. The advantages of this method are simplicity and efficiency, solvent-free reaction, atomic economy, meeting the requirements of green chemistry development, and the products have wide application value.

Key words: 2-aminobenzaldehyde, chromone-3-carboxaldehyde, (2-hydroxyphenyl)(3-quinoline)ketone, grind

Cite this article

Qiuling Xu, Ruifen Sun, Junliang Wang, Xiaoshan He. Mechanochemical Synthesis of (2-Hydroxyphenyl)(3- quinolinyl)ketone[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2416-2424.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 31

[1]	Tabassum R.; Ashfaq M.; Oku H. Mini-Rev. Med. Chem. 2021, 21, 1152.
[2]	Dib M.; Ouchetto H.; Ouchetto K. Curr. Org. Synth. 2021, 18, 248.
[3]	El-Hadidy S. A.; Selim Y. A. J. Heterocycl. Chem. 2018, 55, 103.
[4]	Behalo M. S.; Mele G. J. Heterocycl. Chem. 2017, 54, 295.
[5]	Gurjar V. K.; Pal D. Int. J. Pharm. Pharm. Sci. 2019, 11, 17.
[6]	Bhatnagar A.; Pemawat G. Bioorg. Chem. 2024, 153, 107780.
[7]	Yadav P.; Shah K. Bioorg. Chem. 2021, 109, 104639.
[8]	Wang Z. X.; Xu H. X.; Han X. Z.; Fan S. X.; Zhu J. Org. Lett. 2024, 26, 8559.
[9]	Shi P. F.; Wang L. L.; Guo S.; Chen K. H.; Wang J.; Zhu J. Org. Lett. 2017, 19, 4359.
[10]	Wang L.; Shen Q.; Yu J. J.; Liu M. T.; Qiu J.; Fang L.; Guo F. L.; Tang J. Synthesis 2012, 44, 389.
[11]	Friščić T.; Mottillo C.; Titi H. M. Angew. Chem., Int. Ed. 2019, 59, 1018.
[12]	Krusenbaum A.; Grätz S.; Tigineh G. T.; Borchardt L.; Kim J. G. Chem. Soc. Rev. 2022, 51, 2873. doi: 10.1039/d1cs01093j pmid: 35302564
[13]	Bhutia Z. T.; Prasannakumar G.; Das A.; Biswas M.; Chatterjee A.; Banerjee M. ChemistrySelect 2017, 2, 1183.
[14]	Achar T. K.; Bose A.; Mal P. Beilstein J. Org. Chem. 2017, 13, 1907.
[15]	Sim Y.; Shi Y. X.; Ganguly R.; Li Y. X.; García F. Chem.-Eur. J. 2017, 23, 11279.
[16]	Howard J. L.; Nicholson W.; Sagatov Y.; Browne D. L. Beilstein J. Org. Chem. 2017, 13, 1950.
[17]	Yang T. L.; Nie Z. W.; Su M. D.; Li H.; Luo W. P.; Liu Q.; Guo C. C. J. Org. Chem. 2021, 86, 15228.
[18]	Zeghada S.; Bentabed-Ababsa G.; Mongin O.; Erb W.; Picot L.; Thiéry V.; Roisnel T.; Dorcet V.; Mongin F. Tetrahedron 2020, 76, 131435.
[19]	Kishore P. S.; Gujjarappa R.; Rama Kishore Putta V. P.; Polina S.; Singh V.; Malakar C. C.; Pujar P. P. ChemistrySelect 2022, 7, e202204238.
[20]	Zeng D. S.; Yang T. B.; Tang N.; Deng W.; Xiang J. N.; Yin S.-F.; Kambe N.; Qiu R. H. Synthesis 2022, 54, 2361.
[21]	Bhanage B.; Deshmukh D. Synlett 2018, 29, 979.
[22]	Reis J.; Gaspar A.; Milhazes N.; Borges F. J. Med. Chem. 2017, 60, 7941.
[23]	Amen Y.; Elsbaey M.; Othman A.; Sallam M.; Shimizu K. Molecules 2021, 26, 7646.
[24]	Semwal R. B.; Semwal D. K.; Combrinck S.; Viljoen A. Phytochem. Rev. 2020, 19, 761.
[25]	El-Helw E. A. E.; El-Badawy A. A. J. Heterocycl. Chem. 2020, 57, 2354.
[26]	Langer P. Synlett 2022, 33, 207.
[27]	Duan Y.-d.; Jiang Y.-Y.; Guo F.-X.; Chen L.-X.; Xu L.-L.; Zhang W.; Liu B. Fitoterapia 2019, 135, 114.
[28]	Silva C. F. M.; Pinto D. C. G. A.; Silva A. M. S. ChemMedChem 2016, 11, 2252.
[29]	Bao W.; Wang J.-Q.; Xu X.-T.; Zhang B.-H.; Liu W.-T.; Lei L.-S.; Liang H.; Zhang K.; Wang S.-H. Chem. Commun. 2018, 54, 8194.
[30]	Jiang B.-J.; Zhang S.-L. Adv. Synth. Catal. 2022, 364, 2157.
[31]	El-Sayed T.; Aboelnaga A.; El-Atawy M.; Hagar M. Molecules 2018, 23, 1348.

Entry	Base (mmoL)	Temperature/℃	Yield^b/%
1	Et₃N (0.15)	80	98
2	DIPEA (0.15)	80	90
3	DIPA (0.15)	80	82
4	Piperidine (0.15)	80	52
5	DBU (0.15)	80	71
6	K₂CO₃ (0.15)	80	34
7	K₃PO₄ (0.15)	80	34
8	TMG (0.15)	80	99
9	TMG (0.10)	80	77
10	TMG (0.05)	80	75
11	TMG (0.15)	60	34
12	TMG (0.15)	40	10
13	TMG (0.15)	25	NR
14^c	TMG (0.15)	80	61
15^d	TMG (0.15)	80	54
16^e	TMG (0.15)	80	68
17^f	TMG (0.15)	80	90
18^g	TMG (0.15)	80	73

Entry	Base (mmoL)	Temperature/℃	Yield^b/%
1	Et₃N (0.15)	80	98
2	DIPEA (0.15)	80	90
3	DIPA (0.15)	80	82
4	Piperidine (0.15)	80	52
5	DBU (0.15)	80	71
6	K₂CO₃ (0.15)	80	34
7	K₃PO₄ (0.15)	80	34
8	TMG (0.15)	80	99
9	TMG (0.10)	80	77
10	TMG (0.05)	80	75
11	TMG (0.15)	60	34
12	TMG (0.15)	40	10
13	TMG (0.15)	25	NR
14^c	TMG (0.15)	80	61
15^d	TMG (0.15)	80	54
16^e	TMG (0.15)	80	68
17^f	TMG (0.15)	80	90
18^g	TMG (0.15)	80	73

机械化学合成(2-羟基苯基)(3-喹啉基)甲酮

Mechanochemical Synthesis of (2-Hydroxyphenyl)(3- quinolinyl)ketone

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 31

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wang Kehu, Yin Xuejiao, Tao Rui, Huang Danfeng, Su Yingpeng, Hu Yulai, Fu Ying, Du Zhengyin, Wang Jinxian. Study on the Grinding-Induced Solvent-Free Preparation of 3-Styryl-1,5-diketones [J]. Chin. J. Org. Chem., 2016, 36(1): 113-120.
[2]	Wu Lihuan, Guo Haifu, Wang Xinyi, Wu Ruifen . Synthesis and Structure Characterization of Novel 3-Substituted-(thio)chroman-4-one Derivatives [J]. Chin. J. Org. Chem., 2012, (03): 608-611.
[3]	DIAO Xiao-Ju, JI Hong-Lou, YIN Shan, RONG Liang-Ce, TU Shu-Jiang. Synthesis of 1,3,5-Triaryl-2-aroylcyclohexanol Derivatives and Crys-tal Structure under Solvent-Free Conditions [J]. Chin. J. Org. Chem., 2011, 31(07): 1064-1068.
[4]	ZHAO Li-Qin, ZHOU Bo, LI Yi-Qun. Synthesis of Spirooxindole Derivatives under Solvent- and Catalyst-Free Conditions [J]. Chin. J. Org. Chem., 2011, 31(04): 553-556.
[5]	LI Ji-Tai, SUN Ming-Xuan, HE Gen-Ye. Synthesis of 5-Arylmethylene Barbituric Acid Catalyzed by p-Toluene Sulfonic Acid Using Grinding Method [J]. Chin. J. Org. Chem., 2011, 31(01): 123-125.
[6]	Rong, Liangce^*,a,b ; Han, Hongxia^a; Jiang, Hong^b; Zhuang, Qiya ^a; Wang, Suhui^a; Tu, Shujiang ^a,b . Synthesis of 6-Amino-8-aryl-2-methyl-5,7,7(1H)-tricarbonitrile-2,3,8,8a- tetrahydroisoquinoline Derivatives under Solvent-Free Conditions Using a Ginding Method [J]. Chin. J. Org. Chem., 2009, 29(06): 962-965.
[7]	Xu, Huajian; Xu, Xiaolan; Feng, Yisi*. A Novel Reaction of 10-Methylacridinium with Reactive Metals under Grinding [J]. Chin. J. Org. Chem., 2009, 29(02): 289-291.
[8]	LI, Ji-Tai* ; LIN, Zhi-Ping. Synthesis of Bis(indol-3-yl)methanes Catalyzed by Montmorillonite K10-ZnCl2 by Grinding [J]. Chin. J. Org. Chem., 2008, 28(07): 1238-1242.
[9]	XIE Wen-Lin*<sup>,<i>a</sup></i>, XIAO Gui-Wu<i><sup>b</sup></i>, GU Lian-Quan<i><sup>b</sup></i>. Solvent-Free Synthesis of 5,6-Disubstituted-pyridine-2,3-diones [J]. Chin. J. Org. Chem., 2008, 28(06): 1123-1125.
[10]	ZHANG Hui*, CAO Wei-Guo, REN Zhong-Jiao. Solvent-Free One-Pot Process for the Synthesis of Tetrahydro-benzo[b]-γ-pyran Derivatives under Grinding [J]. Chin. J. Org. Chem., 2007, 27(08): 1018-1021.
[11]	LI Lei,REN Zhong-Jiao*,CAO Wei-Guo,HUANG Pei-Gang,ZHU Hua. Solvent-Free Darzens Condensation Reaction of AromaticAldehydes with Phenacyl Chloride by Grinding [J]. Chin. J. Org. Chem., 2007, 27(01): 120-122.
[12]	TIAN Da-Nian,LIU Wan-Yi*. Solid Phase Carrizaro Reaction under Al₂O₃/NaOH through Grinding Method [J]. Chin. J. Org. Chem., 2006, 26(11): 1525-1528.
[13]	JIN Tong-Shou*,ZHAO Ying,LIU Li-Bin,LI Tong-Shuang. Synthesis of 1,2,3,6-Tetrahydropyrimidin-2-one Derivatives by Grinding Method [J]. Chin. J. Org. Chem., 2006, 26(07): 975-978.
[14]	WANG Chang-Qing,REN Zhong-Jiao*,CAO Wei-Guo TONG Wei-Qi,WANG Gao-Ping. Synthesis of Arylidene Meldrum’s Acids via the Knoevenagel Condensation Reaction under Grinding [J]. Chin. J. Org. Chem., 2006, 26(01): 107-109.
[15]	GENG Li-Jun*^,1,2,LI Ji-Tai²,WANG Shu-Xiang ². Application of Grinding Method to Solid-state Organic Synthesis [J]. Chin. J. Org. Chem., 2005, 25(05): 608-613.