Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives

doi:10.6023/cjoc202308010

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 644-649.DOI: 10.6023/cjoc202308010 Previous Articles Next Articles

4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成

高宝昌^a^,^b^,^*(), 石雨^b, 田媛^b, 张治国^b, 张婧如^b, 孙宇峰^b, 毛国梁^a, 戴凌燕^c^,^*()

a 东北石油大学化学化工学院黑龙江大庆 163319
b 黑龙江省科学院大庆分院植物化学研究所黑龙江大庆 163319
c 黑龙江八一农垦大学生命科学技术学院黑龙江大庆 163319

收稿日期:2023-08-12 修回日期:2023-10-13 发布日期:2023-11-07
基金资助:
黑龙江省自然科学基金(LH2020B022); 黑龙江省科学院院长基金(YZ2022DQ01); 黑龙江省科学院双提雁阵特别计划基金(YZQY2023DQ01); 黑龙江省省属科研院所科研业务费基金(YS2023DQ02)

Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives

Baochang Gao^a^,^b(), Yu Shi^b, Yuan Tian^b, Zhiguo Zhang^b, Jingru Zhang^b, Yufeng Sun^b, Guoliang Mao^a, Lingyan Dai^c()

a College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing, Heilongjiang 163319
b Institute of Phytochemistry, Daqing Branch of Heilongjiang Academy of Sciences, Daqing, Heilongjiang 163319
c College of Science and Biotechnology, Heilongjiang Bayi Agricultural University, Daqing, Heilongjiang 163319

Received:2023-08-12 Revised:2023-10-13 Published:2023-11-07
Contact: * E-mail: chemgbc@163.com; dailingyan770416@126.com
Supported by:
Heilongjiang Provincial Natural Science Foundation(LH2020B022); Dean Foundation of Heilongjiang Academy of Sciences(YZ2022DQ01); Shuangtiyanzhen Special Plan Foundation of Heilongjiang Academy of Sciences(YZQY2023DQ01); Institutes Scientific Research Foundation of Heilongjiang Provincial Scientific Research(YS2023DQ02)

2-Pyrone derivatives have demonstrated considerable potential for usage in the field of medicine. Many of these skeleton structures have been used as precursors in the synthesis of pharmacologically active molecules. As a result, it is critical to explore new approaches for the synthesis of 2-pyrones. A series of 2-pyrone derivatives were synthesized from β-oxo amides and ethyl cyanoacetate through one-step reaction. The methodology offers several significant advantages including mild conditions, ease of handling, and high yields (82%~93%). Such, an efficient synthesis approach for 2-pyrones is provided.

Key words: 2-pyrones, β-oxo amides, cyclization

Cite this article

Baochang Gao, Yu Shi, Yuan Tian, Zhiguo Zhang, Jingru Zhang, Yufeng Sun, Guoliang Mao, Lingyan Dai. Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 644-649.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 5

References 22

[1]	(a) Vara Prasad, J. V. N.; Para, K. S.; Lunney, E. A.; Ortwine, D. F.; Dunbar, J. B., Jr.; Ferguson, D.; Tummino, P. J.; Hupe, D.; Tait, B. D.; Domagala, J. M.; Humblet, C.; Bhat, T. N.; Liu, B.; Guerin, D. M. A.; Baldwin, E. T.; Erickon, J. W.; Swayer, T. K. J. Am. Chem. Soc. 1994, 116, 6989. doi: 10.1021/ja00094a085 pmid: 9371233
	(b) Douglas, C. J.; Sklenicka, H. M.; Shen, H. C.; Mathias, D. S.; Degen, S. I.; Golding, G. M.; Morgan, C. D.; Shih, R. A.; Mueller, K. L.; Seurer, I. M.; Johnson, E. W.; Hsung, R. P. Tetrahedro. 1999, 55, 13683. doi: 10.1016/S0040-4020(99)00847-9 pmid: 9371233
	(c) Hagen, S. E.; Vara Prasad, J. V. N.; Boyer, F. E.; Domagala, J. M.; Ellsworth, E. L.; Gjda, C.; Hamilton, H. W.; Markkoski, L. J.; Steinbangh, B. A.; Tit, B. D.; Lunney, E. A.; Tummino, P. J.; Fergnson, D.; Hupe, D.; Nouhan, C.; Gracheck, S. J.; Saunders, J. M.; Vander Roest, S. J. Med. Chem. 1997, 40, 3707. pmid: 9371233
[2]	(a) Claydon, N.; Allan, M. Trans. Br. Mycol. Soc. 1987, 88, 503. doi: 10.1016/S0007-1536(87)80034-7
	(b) Simon, A.; Dunlop, R. W.; Ghisalberti, E. L.; Silvasithamparam, K. Soil Biol. Biochem. 1988, 20, 263. doi: 10.1016/0038-0717(88)90050-8
	(c) You, X. K.; Lin, Z. L.; Zhang, X. L.; Gao, Y. Chin. J. Org. Chem. 2012, 32, 156 (in Chinese). doi: 10.6023/cjoc1104071
	(游新奎, 林志兰, 张雪利, 高原, 有机化学. 2012, 32, 156.) doi: 10.6023/cjoc1104071
[3]	Liu, Z.; Meinwald, J. J. Org. Chem. 1996, 61, 6693. doi: 10.1021/jo951394t
[4]	Aytemir, M. D.; Calis, U.; Ozalp, M. Arch. Pharm. Med. Chem. 2004, 337, 281. doi: 10.1002/ardp.v337:5
[5]	(a) Yao, T.; Larock, R. C. J. Org. Chem. 2003, 68, 5936. doi: 10.1021/jo034308v
	(b) Fairlamb, I. J. S.; Marrison, L. R.; Dickinson, J. M.; Lu, F. J.; Schmidt, J. P. Bioorg. Med. Chem. 2004, 12, 4285. doi: 10.1016/j.bmc.2004.01.051
[6]	Shi, X.; Leal, W. S.; Liu, Z.; Schrader, E.; Meinwald, J. Tetrahedron Lett. 1995, 36, 71. doi: 10.1016/0040-4039(94)02214-V
[7]	Allen M. Chem. Br. 1996, May, 35.
[8]	Kondoh, M.; Usui, T.; Kobayashi, S.; Tsuchiya, K.; Nishikawa, K.; Nishikiori, T.; Mayumi, T.; Osada, H. Cancer Lett. 1998, 126, 29. pmid: 9563645
[9]	Kobayashi, S.; Tsuchiya, K.; Kurokawa, T.; Nakagawa, T.; Shimada, N.; Iitaka, Y. J. Antibiot. 1994, 47, 703. pmid: 7794417
[10]	Tsuchiya, K.; Kobayashi, S.; Nishikiori, T.; Nakagawa, T.; Tatsuta, K. J. Antibiot. 1997, 50, 259. pmid: 9127198
[11]	(a) Ichihara, A.; Tazaki, H.; Sakamura, S. Tetrahedron Lett. 1983, 48, 5373.
	(b) Chmielewski, M.; Jurczak, J. J. Org. Chem. 1981, 46, 2230. doi: 10.1021/jo00324a008
	(c) Hernandez-Galan, R. J.; Salva, R.; Massannet, G. M.; Collado, I. G. Tetrahedro. 1993, 49, 1701.
[12]	Atul, G.; Vishnu, J. R. Tetrahedro. 2009, 65, 7865. doi: 10.1016/j.tet.2009.06.031
[13]	Xu, M. M.; Cai, Q. Chin. J. Org. Chem. 2022, 42, 698 (in Chinese). doi: 10.6023/cjoc202109025
	(徐萌萌, 蔡泉, 有机化学. 2022, 42, 698.) doi: 10.6023/cjoc202109025
[14]	(a) Benetti, S.; Romagnoli, R.; De Risi, C.; Spalluto, G.; Zanirato, V. Chem. Rev. 1995, 95, 1065. doi: 10.1021/cr00036a007
	(b) Bonne, D.; Coquerel, Y.; Constantieux, T.; Rodriguez, J. Tetrahedron: Asymmetr. 2010, 21, 1085. doi: 10.1016/j.tetasy.2010.04.045
	(c) del Duque, M. M. S.; Allais, C.; Isambert, N.; Constantieux, T.; Rodriguez, J. In Synthesis of Heterocycles via Multicomponent Reactions I, Eds.: Orru, R. V. A.; Ruijter, E.,Springer Berlin Heidelberg, 2010, p. 227.
	(d) Liang, Y. J.; Huang, P.; Zhang, R.; Dong, D. W. Chin. J. Org. Chem. 2014, 34, 1037 (in Chinese). doi: 10.6023/cjoc201403006
	(梁永久, 黄鹏, 张睿, 董德文, 有机化学. 2014, 34, 1037.) doi: 10.6023/cjoc201403006
[15]	(a) Zhang Z. Ph.D. Dissertation. Northeast Normal University, Changchun, 2010 (in Chinese). pmid: 21391701
	(张志国, 博士论文,东北师范大学, 长春, 2010.) pmid: 21391701
	(b) Xiang, D.; Wang, K.; Liang, Y.; Zhou, G.; Dong, D. Org. Lett. 2008, 10, 345. doi: 10.1021/ol702846t pmid: 21391701
	(c) Zhang, Z.; Zhang, Q.; Sun, S.; Xiong, T.; Liu, Q. Angew. Chem.. Int. Ed. 2007, 46, 1726. doi: 10.1002/anie.v46:10 pmid: 21391701
	(d) Wang, K.; Xiang, D.; Liu, J.; Pan, W.; Dong, D. Org. Lett. 2008, 10, 1691. doi: 10.1021/ol800178x pmid: 21391701
	(e) Zhang, R.; Liang, Y.; Zhou, G.; Wang, K.; Dong, D. J. Org. Chem. 2008, 73, 8089. doi: 10.1021/jo801289p pmid: 21391701
	(f) Xiang, D.; Yang, Y.; Zhang, R.; Liang, Y.; Pan, W.; Huang, J.; Dong, D. J. Org. Chem. 2007, 72, 8593. doi: 10.1021/jo7015482 pmid: 21391701
	(g) Zhang, R.; Zhang, D.; Guo, Y.; Zhou, G.; Jiang, Z.; Dong, D. J. Org. Chem. 2008, 73, 9504. doi: 10.1021/jo801959j pmid: 21391701
	(h) Zhang, R.; Zhang, D.; Liang, Y.; Zhou, G.; Dong, D. J. Org. Chem. 2011, 76, 2880. doi: 10.1021/jo101949y pmid: 21391701
[16]	(a) Gao, B. C.; Sun, Y. F.; Wang, J.; Zu, L. W.; Zhang, X.; Liu, W. B. J. Heterocycl. Chem. 2018, 55, 2732. doi: 10.1002/jhet.v55.12
	(b) Gao, B. C.; Sun, Y. F.; Wang, J.; Chang, C.; Yuan, Z. G.; Tian, Y.; Shi, Y.Liu. W. B. J. Heterocycl. Chem. 2019, 56, 2281. doi: 10.1002/jhet.v56.8
	(c) Gao, B. C.; Sun Y. F. Wang, J.; Yuan, Z. G.; Zu, L. W.; Zhang, X.; Liu, W. B. RSC Adv. 2018, 8, 33625. doi: 10.1039/C8RA05709E
	(d) Peter, Z.; Cheuk, K. L. Synlet. 2003, 215.
	(e) Atul, G.; Fateh, V. S.; Ashoke, S.; Prakas, R. M. Synlett. 2005, 623.
	(f) Vishnu, K. T.; Hardesh, K. M.; Balendu, K.; Brijesh, K.; Vishnu, J. R. Synlet. 2009, 2992.
[17]	Zhou, Q. F.; Zhao, S.; Wang, X.; Lu, T. Chin. J. Org. Chem. 2010, 30, 1652 (in Chinese).
	(周庆发, 赵慎, 王珣, 陆涛, 有机化学. 2010, 30, 1652.)
[18]	(a) Wang, D. P.; Zhang, X. D.; Liang, Y.; Li, J. H. Chin. J. Org. Chem. 2006, 26, 19 (in Chinese). doi: 10.1002/cjoc.v26:1
	(王德平, 张旭东, 梁云, 李金恒, 有机化学. 2006, 26, 19.)
	(b) Lee, J. H.; Kim, W. S.; Lee, Y. Y.; Cho, C. G. Tetrahedron Lett. 2002, 43, 5779. doi: 10.1016/S0040-4039(02)01182-6
	(c) Kim, W. S.; Kim, H. J.; Cho, C. G. J. Am. Chem. Soc. 2003, 125, 14288. doi: 10.1021/ja037043a
[19]	(a) Wang, Y. F.; Deng, W.; Liu, L.; Guo, Q. X. Chin. J. Org. Chem. 2005, 25, 8 (in Chinese). pmid: 16557307
	(王晔峰, 邓伟, 刘磊, 郭庆祥, 有机化学. 2005, 25, 8.) pmid: 16557307
	(b) Jin, X. Y.; Xiao, Q.; Ju, Y. Chin. J. Org. Chem. 2009, 29, 44 (in Chinese). pmid: 16557307
	(靳玄烨, 肖强, 巨勇, 有机化学. 2009, 29, 44.) pmid: 16557307
	(c) Fairlamb, I. J. S.; Lee, A. F.; Loe-Mie, F. E. M.; Niemelä, E. H.; O'Brien, C. T.; Whitwood, A. C. Tetrahedro. 2005, 61, 9827. doi: 10.1016/j.tet.2005.07.102 pmid: 16557307
	(d) Fairlamb, I. J. S.; O'Brien, C. T.; Lin, Z.; Lam, K. C. Org. Biomol. Chem. 2006, 4, 1213. pmid: 16557307
[20]	(a) Cerezo, S.; Moreno-Maňas, M.; Pleixats, R. Tetrahedro. 1998, 54, 7813. doi: 10.1016/S0040-4020(98)00415-3
	(b) Afarinkia, K.; Berna-Canovas, J. Tetrahedron Lett. 2000, 41, 4955. doi: 10.1016/S0040-4039(00)00744-9
[21]	(a) Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 6295. doi: 10.1021/jo901077r
	(b) Luo, T.; Schreiber, S. L. Angew. Chem.. Int. Ed. 2007, 46, 8250. doi: 10.1002/anie.v46:43
[22]	(a) Zhu, X. F.; Henry, C. E.; Wang, J.; Dudding, T.; Kwon, O. Org. Lett. 2005, 7, 1387. doi: 10.1021/ol050203y pmid: 18537252
	(b) Dudding, T.; Kwon, O.; Mercier, E. Org. Lett. 2006, 8, 3643. doi: 10.1021/ol061095y pmid: 18537252
	(c) Usachev, B. I.; Obydennov, D. L.; Röschenthaler, G. V.; Sosnovskikh, V. Y. Org. Lett. 2008, 10, 2857. doi: 10.1021/ol800992z pmid: 18537252

Entry	Base (equiv.)	Solvent	Temp./℃	Yield/%
1	NaOH (1) or KOH (1)	DMF	r.t.	0 or 0
2	NaOH (1) or KOH (1)	DMF	80	Mixture or mixture
3	CsCO₃(1)	C₂H₅OH	50 or reflux	Mixture or 17
4	LiOH (1)	CH₃OH	50 or reflux	Mixture or 20
5	Pyridine (1)	C₂H₅OH	r.t. or 50	0 or mixture
6	Pyridine (1 or 2)	CH₂Cl₂	r.t.	0 or 0
7	DBU (1)	DMF	r.t. or 70	Mixture or mixture
8	DABCO (1)	C₂H₅OH	r.t. or 50	Mixture or mixture
9	DABCO (2)	CH₃OH	reflux	Mixture
10	K₂CO₃ (1)	DMF	r.t. or 50	Mixture or mixture
11	K₂CO₃ (2)	DMF	80 or 110	23 or 31
12	K₂CO₃ (1)	C₂H₅OH	r.t. or reflux	Mixture or 68
13	K₂CO₃ (2)	C₂H₅OH	reflux	67
14	^tBuOK (1)	DMF or C₂H₅OH	80	31 or 44
15	CH₃ONa (1)	CH₃OH	r.t. or 50	25 or 47
16	CH₃ONa (1)	CH₃OH	reflux	52
17	C₂H₅ONa (1)	C₂H₅OH	r.t. or 50	Mixture or 66
18	C₂H₅ONa (1)	C₂H₅OH	reflux	89
19	C₂H₅ONa (0.5 or 2)	C₂H₅OH	reflux	57 or 85
20	C₂H₅ONa (1)	C₂H₅OH	reflux	90^b

Entry	Base (equiv.)	Solvent	Temp./℃	Yield/%
1	NaOH (1) or KOH (1)	DMF	r.t.	0 or 0
2	NaOH (1) or KOH (1)	DMF	80	Mixture or mixture
3	CsCO₃(1)	C₂H₅OH	50 or reflux	Mixture or 17
4	LiOH (1)	CH₃OH	50 or reflux	Mixture or 20
5	Pyridine (1)	C₂H₅OH	r.t. or 50	0 or mixture
6	Pyridine (1 or 2)	CH₂Cl₂	r.t.	0 or 0
7	DBU (1)	DMF	r.t. or 70	Mixture or mixture
8	DABCO (1)	C₂H₅OH	r.t. or 50	Mixture or mixture
9	DABCO (2)	CH₃OH	reflux	Mixture
10	K₂CO₃ (1)	DMF	r.t. or 50	Mixture or mixture
11	K₂CO₃ (2)	DMF	80 or 110	23 or 31
12	K₂CO₃ (1)	C₂H₅OH	r.t. or reflux	Mixture or 68
13	K₂CO₃ (2)	C₂H₅OH	reflux	67
14	^tBuOK (1)	DMF or C₂H₅OH	80	31 or 44
15	CH₃ONa (1)	CH₃OH	r.t. or 50	25 or 47
16	CH₃ONa (1)	CH₃OH	reflux	52
17	C₂H₅ONa (1)	C₂H₅OH	r.t. or 50	Mixture or 66
18	C₂H₅ONa (1)	C₂H₅OH	reflux	89
19	C₂H₅ONa (0.5 or 2)	C₂H₅OH	reflux	57 or 85
20	C₂H₅ONa (1)	C₂H₅OH	reflux	90^b

Entry	1	R	2	Time/h	Yield/%
1	1a	Ph	2a	4	89^a, 90^b
2	1b	4-ClC₆H₄	2b	4.5	91^a, 87^b
3	1c	2-MeC₆H₄	2c	5	93^a, 91^b
4	1d	2-MeOC₆H₄	2d	4	84^a, 82^b
5	1e	2,4-Me₂C₆H₃	2e	4	82^a, 85^b
6	1f	4-MeOC₆H₄	2f	4.5	87^a, 84^b
7	1g	2-ClC₆H₄	2g	5	86^a, 81^b
8	1h	4-MeC₆H₄	2h	4	90^a, 92^b
9	1i	2,5-(MeO)₂-4-ClC₆H₂	2i	5	83^a, 84^b
10	1j	CH₃	2j	5	0

Entry	1	R	2	Time/h	Yield/%
1	1a	Ph	2a	4	89^a, 90^b
2	1b	4-ClC₆H₄	2b	4.5	91^a, 87^b
3	1c	2-MeC₆H₄	2c	5	93^a, 91^b
4	1d	2-MeOC₆H₄	2d	4	84^a, 82^b
5	1e	2,4-Me₂C₆H₃	2e	4	82^a, 85^b
6	1f	4-MeOC₆H₄	2f	4.5	87^a, 84^b
7	1g	2-ClC₆H₄	2g	5	86^a, 81^b
8	1h	4-MeC₆H₄	2h	4	90^a, 92^b
9	1i	2,5-(MeO)₂-4-ClC₆H₂	2i	5	83^a, 84^b
10	1j	CH₃	2j	5	0

4-甲基-2-氧代-6-芳氨基-二氢-吡喃-3-腈衍生物的合成

Synthesis of 4-Methyl-2-oxo-6-arylamino-2H-pyran-3-carbonitrile Derivatives

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 22

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jing Tang, Wenkun Luo, Jun Zhou. Advances in the Synthesis of Azaspiro[4.5]trienones [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3006-3034.
[2]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[3]	Yuzhuo Chen, Hongmei Sun, Liang Wang, Fangzhi Hu, Shuaishuai Li. Research Progress on Construction of Heterocyclic Skeletons Based on α-Hydride Transfer Strategy [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2323-2337.
[4]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[5]	Lixing Sun, Tingting Sun, Haiqing Wang, Shufang Wu, Xiaoye Wang, Tianya Liu, Yuchen Zhang. Lewis Acid-Catalyzed [2+4] Cyclization of 3-Alkyl-2-vinylindoles with α,β-Unsaturated N-Sulfonyl Ketimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2178-2188.
[6]	Zhijun Ren, Weiwei Luo, Jun Zhou. Recent Progress in Silver-Mediated Tandem Cyclization of N-Arylacrylamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2026-2039.
[7]	Jingpeng Li, Shuntao Huang, Qi Yang, Weiqiang Li, Teng Liu, Chao Huang. A Practical Synthesis of (Z)-N-Vinyl Substituted N,O-Acetals under Continuous Flow Technology [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1550-1558.
[8]	Nan Jiang, Guanjie Huang, Yan Hu, Bo Wang. Ruthenium-Catalyzed C—H [4＋2] Annulation of Quinazolinones with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1537-1549.
[9]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[10]	Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.
[11]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[12]	Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.
[13]	Wenting Wei, Zhuangzhuang Li, Wandi Li, Jiaqi Li, Xianying Shi. Green Method for Constructing Phthalides via Oxidative Coupling of Aromatic Acids and Acrylates in Neat Water and Air [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1177-1186.
[14]	Xiaoting Qin, Ning Zou, Caimei Nong, Dongliang Mo. Recent Advances on the Synthesis of Nine-Membered N-Heterocycles [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 130-155.
[15]	Donghan Liu, Xihang Lu, Zhangmengjie Chai, Haoqi Yang, Yulin Sun, Fuchao Yu. Progress in Construction of 2H-Pyrrol-2-ones Skeleton [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 57-73.