Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety

doi:10.6023/cjoc202007068

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (2): 738-756.DOI: 10.6023/cjoc202007068 Previous Articles Next Articles

Article

含6-氟喹唑啉片段的新型1,3,4-噁(噻)二唑类衍生物的合成及抗菌活性研究

石军¹, 罗娜¹, 丁慕晗¹, 李传会¹, 万苏然¹, 李培甲¹, 李君荭¹, 鲍小平¹^,^*()

1 贵州大学精细化工研究开发中心绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与农业生物工程重点实验室贵阳 550025

收稿日期:2020-07-29 修回日期:2020-08-11 发布日期:2020-09-16
通讯作者: 鲍小平
作者简介:
* Corresponding author. E-mail: baoxp_1980@aliyun.com
基金资助:
贵州省自然科学基金(20201Z025); 贵州省教育厅科技拔尖人才支持计划(2018038); 贵州省高层次留学人才创新创业(201809)

Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety

Jun Shi¹, Na Luo¹, Muhan Ding¹, Chuanhui Li¹, Suran Wan¹, Peijia Li¹, Junhong Li¹, Xiaoping Bao¹^,^*()

1 State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2020-07-29 Revised:2020-08-11 Published:2020-09-16
Contact: Xiaoping Bao
Supported by:
the Natural Science Foundation of Guizhou Province(20201Z025); the Young Top-Notch Talent Support Program of Guizhou Provincial Education Department(2018038); the Guizhou Provincial High-Level Overseas Talents Innovation and Entrepreneurship Program(201809)

1. cjoc202007068.pdf(9221KB)

Abstract

To search efficient agricultural antimicrobial lead compounds, fifty 1,3,4-oxa(thia)diazole derivatives 6a~6y and 8a~8y containing 6-fluoroquinazoline moiety were designed, synthesized and evaluated for their antimicrobial activities, based on the method of the splicing of bioactive substructures. The structures of target compounds were fully characterized by ¹H NMR, ¹³C NMR, and HRMS spectra, and two compounds 6i and 8x were further confirmed via single crystal X-ray diffraction analysis. The preliminary bioassays revealed that some compounds exhibited good antifungal activity in vitro. For example, compounds 6b, 6d, 6t, 6v and 6x were found to have the inhibition rates of 58%, 58%, 55%, 63% and 60% against Gibberella zeae at 50 μg/mL, respectively. Additionally, compounds 6v and 8v displayed the inhibition efficacies of 71% and 64% against Cytospora mandshurica at 50 μg/mL, respectively. Moreover, compound 6v demonstrated an inhibition rate of 72% against Colletotrichum gloeosporioides at 50 μg/mL. The above activities were all better than that of control agent Hymexazol (51%, 61%, and 70%, respectively). Finally, some compounds also showed certain inhibition potencies in vitro against tested bacteria at 100 μg/mL.

Key words: 1,3,4-oxadiazole, 1,3,4-thiadiazole, 6-fluoroquinazoline, synthesis, antimicrobial activity

Cite this article

Jun Shi, Na Luo, Muhan Ding, Chuanhui Li, Suran Wan, Peijia Li, Junhong Li, Xiaoping Bao. Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety[J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 738-756.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 25

[1]	Li D.; Zhang S.; Song Z.; Wang G.; Li S. Eur. J. Med. Chem. 2017, 136, 114. doi: 10.1016/j.ejmech.2017.04.073
[2]	Wang L.; Li C.; Zhang Y.; Qiao C.; Ye Y. J. Agric. Food Chem. 2013, 61, 8632. doi: 10.1021/jf402388x
[3]	Price C.L.; Parker J.E.; Warrilow A. G. S.; Kelly D.E.; Kelly S.L. Pest Manage. Sci. 2015, 71, 1054. doi: 10.1002/ps.4029
[4]	Mansfield J.; Genin S.; Magori S.; Citovsky V.; Sriariyanum M.; Ronald P.; Dow M.; Verdier V.; Beer S.V.; Machado M.A.; Toth I.; Salmond G.; Foster G.D. Mol. Plant Pathol. 2012, 13, 614. doi: 10.1111/mpp.2012.13.issue-6
[5]	Yang L.; Bao X.P. RSC Adv. 2017, 7, 34005. doi: 10.1039/C7RA04819J
[6]	Zhang M.; Dai Z.C.; Qian S.S.; Liu J.Y.; Xiao Y.; Lu A.M.; Zhu H.L.; Wang J.X.; Ye Y.H. J. Agric. Food Chem. 2014, 62, 9637. doi: 10.1021/jf504359p
[7]	Khan I.; Ibrar A.; Abbas N.; Saeed A. Eur. J. Med. Chem. 2014, 76, 193. doi: 10.1016/j.ejmech.2014.02.005
[8]	Fan Z.; Shi J.; Bao X. Mol. Diversity 2018, 22, 657. doi: 10.1007/s11030-018-9821-8
[9]	Shi J.; Luo N.; Ding M.; Bao X. Chin. Chem. Lett. 2020, 31, 434. doi: 10.1016/j.cclet.2019.06.037
[10]	Opoku-Temeng C.; Naclerio G.A.; Mohammad H.; Dayal N.; Abutaleb N.S.; Seleem M.N.; Sintim H.O. Eur. J. Med. Chem. 2018, 155, 797. doi: S0223-5234(18)30514-2 pmid: 29957525
[11]	Cui Z.M.; Li Y.S.; Hu D.K.; Tian H.; Jiang J.Z.; Wang Y.; Yan X.J. Sci. Rep. 2016, 6, 20204. doi: 10.1038/srep20204
[12]	Wu W.; Fei Q.; He J.; Liu L.; Ouyang G. Chem. Bull. 2019, 82, 74. (in Chinese)
	吴文能, 费强, 何军, 刘雷, 欧阳贵平, 化学通报, 2019, 82, 74.).
[13]	Zhang Y.; Liu X.H.; Zhan Y.Z.; Zhang L.Y.; Li Z.M.; Li Y.H.; Zhang X.; Wang B.L. Bioorg. Med. Chem. Lett. 2016, 26, 4661. doi: 10.1016/j.bmcl.2016.08.059
[14]	Wang T.; Miao W.; Wu S.; Bing G.; Zhang X.; Qin Z.; Yu H.; Qin X.; Fang J. Chin. J. Chem. 2011, 29, 959. doi: 10.1002/cjoc.201190196
[15]	Chen J.; Chen Y.; Gan X.; Song B.; Hu D.; Song B. J. Agric. Food Chem. 2018, 66, 9616. doi: 10.1021/acs.jafc.8b03020
[16]	Han F.; Wan R.; Wang Y.; Wang P.; Wang J. Chin. J. Org. Chem. 2010, 30, 132. (in Chinese)
	韩峰, 万嵘, 王瑶, 王朋, 王锦堂, 有机化学, 2010, 30, 132.).
[17]	Chen X.; Gan X.; Chen J.; Chen Y.; Wang Y.; Hu D.; Song B. Chin. J. Org. Chem. 2017, 37, 2343. (in Chinese) doi: 10.6023/cjoc201703022 pmid: 4013A66C-29E4-4C33-97B0-76454608F358
	陈学文, 甘秀海, 陈吉祥, 陈永中, 王艳娇, 胡德禹, 宋宝安, 有机化学, 2017, 37, 2343.). doi: 10.6023/cjoc201703022 pmid: 4013A66C-29E4-4C33-97B0-76454608F358
[18]	Yan L.; Li Y.; Deng M.; Chen A.; Du Z.; Dong C.; Chen H. Chin. J. Org. Chem. 2020, 40, 731. (in Chinese) doi: 10.6023/cjoc201907052 pmid: 32e327ce-834d-4a95-9fcd-1a877fcad60c
	鄢龙家, 黎永良, 邓明高, 陈安超, 杜志云, 董长治, 陈惠雄, 有机化学, 2020, 40, 731.). doi: 10.6023/cjoc201907052 pmid: 32e327ce-834d-4a95-9fcd-1a877fcad60c
[19]	Nazir M.; Abbasi M.A.; Rehman A.; Siddiqui S.Z.; Khan K.M.; Kanwal; Salar, U.; Shahi, M.; Ashraf, M.; Lodhi, M.A.; Khan, F.A.Bioorg. Chem. 2018, 81, 253. doi: 10.1016/j.bioorg.2018.08.010
[20]	Xu G.F.; Song B.A.; Bhadury P.S.; Yang S.; Zhang P.Q.; Jin L.H.; Xue W.; Hu D.Y.; Lu P. Bioorg. Med. Chem. 2007, 15, 3768. doi: 10.1016/j.bmc.2007.03.037
[21]	Luo H.; Hu D.; Wu J.; He M.; Jin L.; Yang S.; Song B. Int. J. Mol. Sci. 2012, 13, 6730. doi: 10.3390/ijms13066730
[22]	Embrechts W.; Herschke F.; Pauwels F.; Stoops B.; Last S.; Pieters S.; Pande V.; Pille G.; Amssoms K.; Smyej I.; Dhuyvetter D.; Scholliers A.; Mostmans W.; Van Dijck K.; Van Schoubroeck B.; Thone T.; De Pooter D.; Fanning G.; Jonckers T. H. M.; Horton H.; Raboisson P.; McGowan D. J. Med. Chem. 2018, 61, 6236. doi: 10.1021/acs.jmedchem.8b00643
[23]	Zayed M.F.; Ihmaid S.K.; Ahmed H. E. A.; El-Adl K.; Asiri A.M.; Omar A.M. Molecules 2017, 22, 188. doi: 10.3390/molecules22020188
[24]	Vitaku E.; Smith D.T.; Njadarson J.T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b
[25]	Fan Z.; Shi J.; Luo N.; Ding M.; Bao X. J. Agric. Food Chem. 2019, 67, 11598. doi: 10.1021/acs.jafc.9b04733

Compd.	Inhibition rate^a/%			Compd.	Inhibition rate^a/%
Compd.	GZ^c	CG^c	CM^c	Compd.	GZ^c	CG^c	CM^c
6a	40±2	20±1	17±2	8a	45±1	47±1	50±1
6b	58±2	42±0	45±0	8b	31 ± 1	34±1	40±1
6c	11±0	16±2	15±3	8c	30 ± 2	32±2	33±2
6d	58±2	52±1	55±2	8d	26±1	29±2	33±2
6e	40±2	13±1	15±3	8e	32±1	7±1	18±2
6f	43±2	11±1	18±1	8f	25±1	16±2	18±2
6g	22±1	14±2	16±0	8g	19±1	32±1	34±2
6h	37±2	13±1	17±3	8h	28±1	23±3	22±3
6i	52±1	29±2	30±3	8i	30±1	19±3	18±1
6j	9±1	22±3	13±2	8j	28±1	28±2	27±1
6k	34±3	22±1	25±2	8k	0	9±2	9±2
6l	38±1	26±3	26±2	8l	21±1	23±3	21±2
6m	0	0	8±3	8m	13±3	21±1	17±1
6n	43±3	24±1	25±2	8n	16±1	15±3	22±3
6o	37±2	13±2	8±1	8o	0	15±1	22±3
6p	31±1	6±2	10±2	8p	0	0	0
6q	43±1	25±2	29±3	8q	31±1	7±2	10±1
6r	34±1	0	9±3	8r	12±1	16±3	15±3
6s	43±1	21±0	26±1	8s	20±1	7±2	9±2
6t	55±3	43±2	47±1	8t	46±1	36±2	44±1
6u	51±2	21±1	19±2	8u	11±1	21±2	25±2
6v	63±1	72±1	71±1	8v	54±1	50±2	64±2
6w	16±2	13±2	13±2	8w	17±3	22±2	14±3
6x	60±2	33±2	45±0	8x	16±1	15±2	21±3
6y	16±3	11±2	31±4	8y	26±1	23±2	24±2
Hymexazol^b	51±1	70±1	61±1

Compd.	Inhibition rate^a/%			Compd.	Inhibition rate^a/%
Compd.	GZ^c	CG^c	CM^c	Compd.	GZ^c	CG^c	CM^c
6a	40±2	20±1	17±2	8a	45±1	47±1	50±1
6b	58±2	42±0	45±0	8b	31 ± 1	34±1	40±1
6c	11±0	16±2	15±3	8c	30 ± 2	32±2	33±2
6d	58±2	52±1	55±2	8d	26±1	29±2	33±2
6e	40±2	13±1	15±3	8e	32±1	7±1	18±2
6f	43±2	11±1	18±1	8f	25±1	16±2	18±2
6g	22±1	14±2	16±0	8g	19±1	32±1	34±2
6h	37±2	13±1	17±3	8h	28±1	23±3	22±3
6i	52±1	29±2	30±3	8i	30±1	19±3	18±1
6j	9±1	22±3	13±2	8j	28±1	28±2	27±1
6k	34±3	22±1	25±2	8k	0	9±2	9±2
6l	38±1	26±3	26±2	8l	21±1	23±3	21±2
6m	0	0	8±3	8m	13±3	21±1	17±1
6n	43±3	24±1	25±2	8n	16±1	15±3	22±3
6o	37±2	13±2	8±1	8o	0	15±1	22±3
6p	31±1	6±2	10±2	8p	0	0	0
6q	43±1	25±2	29±3	8q	31±1	7±2	10±1
6r	34±1	0	9±3	8r	12±1	16±3	15±3
6s	43±1	21±0	26±1	8s	20±1	7±2	9±2
6t	55±3	43±2	47±1	8t	46±1	36±2	44±1
6u	51±2	21±1	19±2	8u	11±1	21±2	25±2
6v	63±1	72±1	71±1	8v	54±1	50±2	64±2
6w	16±2	13±2	13±2	8w	17±3	22±2	14±3
6x	60±2	33±2	45±0	8x	16±1	15±2	21±3
6y	16±3	11±2	31±4	8y	26±1	23±2	24±2
Hymexazol^b	51±1	70±1	61±1

Compd.	Xanthomonas axonopodis pv. citri		Xanthomonas oryzae pv. oryzae		Ralstonia solanacearum
Compd.	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
6a	38±4	33±2	32±3	18±2	9±3	5±3
6b	32±3	16±3	27±3	22±5	21±2	14±3
6c	40±3	30±2	43±3	36±1	20±5	13±4
6d	38±3	28±2	31±3	30±2	14±3	12±5
6e	31±4	27±4	29±3	15±0	18±2	17±1
6f	41±4	25±5	27±4	24±4	17±1	6±3
6g	39±3	20±2	35±1	17±3	21±4	16±2
6h	39±4	29±2	27±1	21±4	28±0	17±4
6i	32±2	30±4	33±6	23±5	33±2	24±3
6j	31±5	26±5	37±3	14±2	18±3	15±2
6k	35±5	24±4	18±5	13±2	27±3	13±4
6l	38±3	27±3	26±3	19±3	47±2	23±3
6m	35±3	20±5	32±5	29±2	17±2	16±2
6n	36±3	26±5	33±3	21±3	25±2	20±3
6o	38±1	27±3	26±2	11±4	29±3	9±4
6p	39±1	30±3	20±4	17±4	19±2	13±5
6q	31±6	21±2	16±5	7±1	15±4	9±3
6r	41±3	28±3	21±3	14±1	26±2	21±3
6s	50±4	37±2	33±2	30±5	17±3	13±3
6t	45±3	32±3	37±5	20±3	26±5	18±3
6u	40±2	30±2	40±4	36±7	33±3	29±3
6v	44±4	34±2	33±1	18±1	34±3	31±5
6w	37±4	28±5	45±5	27±2	35±3	33±3
6x	41±3	33±3	49±4	22±5	30±2	16±2
6y	29±4	21±4	57±2	47±2	48±4	35±3
8a	44±5	27±3	30±6	27±3	25±4	23±3
8b	54±3	32±2	32±4	22±2	34±3	28±3
8c	42±1	35±4	40±1	35±4	22±5	18±4
8d	41±4	32±4	37±1	32±4	44±2	37±4
8e	32±0	29±3	35±2	29±3	48±2	37±1
8f	38±2	29±3	33±5	29±3	49±2	41±3
8g	31±1	26±4	30±8	26±4	36±5	30±4
8h	36±4	29±1	34±3	29±1	20±4	17±4
8i	36±2	31±5	27±6	31±5	28±3	24±1
8j	40±3	38±3	38±8	35±3	66±1	46±1
8k	33±1	30±1	39±3	32±1	29±4	21±4
8l	43±2	31±1	32±8	31±1	35±3	33±2
8m	40±4	28±1	34±4	28±1	24±3	23±3
8n	33±3	30±2	37±3	30±2	17±4	12±6
8o	29±2	20±1	23±8	20±1	22±3	13±3
8p	39±4	28±1	35±8	28±1	21±4	15±4
8q	43±4	30±4	41±0	30±4	33±3	31±2
8r	43±3	31±3	34±5	31±3	40±4	35±4
8s	42±3	39±4	40±2	32±4	30±2	23±7
8t	40±4	34±2	40±3	34±2	34±2	33±5
8u	39±5	31±5	36±4	31±5	30±3	27±3
8v	44±3	25±2	31±3	20±1	28±2	16±4
8w	36±2	29±2	26±3	21±3	24±4	14±2
8x	56±3	52±2	52±3	40±2	56±3	37±4
8y	47±5	35±2	40±4	35±2	32±3	21±1
BMT^b	54±1	37±4	60±2	43±5	50±4	33±2
TDC^b	NT^c	NT^c	NT^c	NT^c	43±3	27±2

Compd.	Xanthomonas axonopodis pv. citri		Xanthomonas oryzae pv. oryzae		Ralstonia solanacearum
Compd.	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL	100 μg/mL	50 μg/mL
6a	38±4	33±2	32±3	18±2	9±3	5±3
6b	32±3	16±3	27±3	22±5	21±2	14±3
6c	40±3	30±2	43±3	36±1	20±5	13±4
6d	38±3	28±2	31±3	30±2	14±3	12±5
6e	31±4	27±4	29±3	15±0	18±2	17±1
6f	41±4	25±5	27±4	24±4	17±1	6±3
6g	39±3	20±2	35±1	17±3	21±4	16±2
6h	39±4	29±2	27±1	21±4	28±0	17±4
6i	32±2	30±4	33±6	23±5	33±2	24±3
6j	31±5	26±5	37±3	14±2	18±3	15±2
6k	35±5	24±4	18±5	13±2	27±3	13±4
6l	38±3	27±3	26±3	19±3	47±2	23±3
6m	35±3	20±5	32±5	29±2	17±2	16±2
6n	36±3	26±5	33±3	21±3	25±2	20±3
6o	38±1	27±3	26±2	11±4	29±3	9±4
6p	39±1	30±3	20±4	17±4	19±2	13±5
6q	31±6	21±2	16±5	7±1	15±4	9±3
6r	41±3	28±3	21±3	14±1	26±2	21±3
6s	50±4	37±2	33±2	30±5	17±3	13±3
6t	45±3	32±3	37±5	20±3	26±5	18±3
6u	40±2	30±2	40±4	36±7	33±3	29±3
6v	44±4	34±2	33±1	18±1	34±3	31±5
6w	37±4	28±5	45±5	27±2	35±3	33±3
6x	41±3	33±3	49±4	22±5	30±2	16±2
6y	29±4	21±4	57±2	47±2	48±4	35±3
8a	44±5	27±3	30±6	27±3	25±4	23±3
8b	54±3	32±2	32±4	22±2	34±3	28±3
8c	42±1	35±4	40±1	35±4	22±5	18±4
8d	41±4	32±4	37±1	32±4	44±2	37±4
8e	32±0	29±3	35±2	29±3	48±2	37±1
8f	38±2	29±3	33±5	29±3	49±2	41±3
8g	31±1	26±4	30±8	26±4	36±5	30±4
8h	36±4	29±1	34±3	29±1	20±4	17±4
8i	36±2	31±5	27±6	31±5	28±3	24±1
8j	40±3	38±3	38±8	35±3	66±1	46±1
8k	33±1	30±1	39±3	32±1	29±4	21±4
8l	43±2	31±1	32±8	31±1	35±3	33±2
8m	40±4	28±1	34±4	28±1	24±3	23±3
8n	33±3	30±2	37±3	30±2	17±4	12±6
8o	29±2	20±1	23±8	20±1	22±3	13±3
8p	39±4	28±1	35±8	28±1	21±4	15±4
8q	43±4	30±4	41±0	30±4	33±3	31±2
8r	43±3	31±3	34±5	31±3	40±4	35±4
8s	42±3	39±4	40±2	32±4	30±2	23±7
8t	40±4	34±2	40±3	34±2	34±2	33±5
8u	39±5	31±5	36±4	31±5	30±3	27±3
8v	44±3	25±2	31±3	20±1	28±2	16±4
8w	36±2	29±2	26±3	21±3	24±4	14±2
8x	56±3	52±2	52±3	40±2	56±3	37±4
8y	47±5	35±2	40±4	35±2	32±3	21±1
BMT^b	54±1	37±4	60±2	43±5	50±4	33±2
TDC^b	NT^c	NT^c	NT^c	NT^c	43±3	27±2

含6-氟喹唑啉片段的新型1,3,4-噁(噻)二唑类衍生物的合成及抗菌活性研究

Synthesis and Antimicrobial Activities of Novel 1,3,4-Oxa(Thia)- diazole Derivatives Containing 6-Fluoroquinazoline Moiety

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 25

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.