Decarboxylative Amidation of Acrylamides with Oxamic Acids

doi:10.6023/cjoc202105025

Abstract

A silver catalyzed decaroxylative amidation of N-arylacrylamides with oxamic acids has been developed. This cascade reaction is an effective way to synthesize various 3,3-disubstitued amide functionalized oxindoles through a sequence of intermolecular carbamoyl radical addition and cyclization in moderate to good yields. This reaction allows a broad range of substrates as well as good functional group compatibility.

Key words: carbamoylation, oxindoles, radical addition cyclization

Cite this article

Qisheng Gao, Qi Jing, Yang Chen, Jing Sun, Mingdong Zhou. Decarboxylative Amidation of Acrylamides with Oxamic Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 257-265.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 14

[1]	(a) Galliford, C. V.; Scheidt, K. A. Angew. Chem. Int. Ed. 2007, 46, 8748. doi: 10.1002/(ISSN)1521-3773
	(b) Zhao, J.-F.; Duan, X.-H.; Peng, L.-N. Chin. J. Org. Chem. 2017, 37, 2498. (in Chinese)
	(赵景峰, 段新华, 郭丽娜, 有机化学, 2017, 37, 2498.) doi: 10.6023/cjoc201705003
	(c) Mai, W.-P.; Wang, J.-T.; Yang, L.-R.; Yuan, J.-W.; Mao, P.; Xiao, Y.-P.; Qu, L.-B. Chin. J. Org. Chem. 2014, 34, 1958. (in Chinese) doi: 10.6023/cjoc201405006
	(买文鹏, 王继涛, 杨亮茹, 袁金伟, 毛璞, 肖咏梅, 屈凌波, 有机化学, 2014, 34, 1958.) doi: 10.6023/cjoc201405006
[2]	(a) Millemaggi, A.; Taylor, R. J. K. Eur. J. Org. Chem. 2010, 4527.
	(b) Leptosin, D.; Takahashi, C.; Numata, A.; Ito, Y.; Matsumura, E.; Araki, H.; Iwaki, H.; Kushida, K. J. Chem. Soc., erkin Trans. 1 1994, 1859.
	(c) Ma, J.; Hecht, S. M. Chem. Commun. 2004, 1190.
[3]	(a) Wong, H.; Yu, P.; Yick, C. Pure Appl. Chem. 1999, 71, 1041. doi: 10.1351/pac199971061041
	(b) Rassu, G.; Zanardi, F.; Battistini, L.; Casriaghi, G. Chem. Soc. Rev. 2000, 29, 109. doi: 10.1039/a900200f
	(c) Xiao, F.; Luo, Y.; Lü, W.; Tang, J. Chin. J. Org. Chem. 2009, 29, 459. (in Chinese)
	(肖锋, 罗宇, 吕伟, 汤杰, 有机化学, 2009, 29, 459.)
	(d) Tian, K.; Meng, J.; Gan, Y.-Y; Li, X.-Q.; Wu, S.-Q.; Chen, J.; Li, W.; Qi, Y.-Y.; Hu, W.-N.; Wang, Z.-C.; Ouyang, G.-P. Chin. J. Org. Chem. 2018, 38, 2657. (in Chinese) doi: 10.6023/cjoc201803051
	(田坤, 孟娇, 甘宜远, 李小琴, 巫受群, 陈洁, 李文, 漆亚云, 胡伟男, 王贞超, 欧阳贵平, 2018, 38, 2657.)
	(e) Boddy, A.; Bull, J. Org. Chem. Front. 2021, 8, 1026. doi: 10.1039/D0QO01085E
	(f) Nakao, Y. Chem. Rev. 2021, 121, 327. doi: 10.1021/acs.chemrev.0c00301
[4]	(a) Jossang, A.; Jossang, P.; Hadi, H.; Sévenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527. doi: 10.1021/jo00023a016
	(b) Stratmann, K.; Moore, R.; Bonjouklian, R.; Deeter, J.; Patterson, G.; Stacey, S.; Smith, C.; Smitka, T. J. Am. Chem. Soc. 1994, 116, 9935. doi: 10.1021/ja00101a015
	(c) Anderton, N.; Cockrum, P.; Colegate, S.; Edgar, J.; Flower, K.; Vit, I.; Willing, R. Phytochemistry 1998, 48, 437. doi: 10.1016/S0031-9422(97)00946-1
	(d) Shi, J.; Yu, J.; Chen, X.; Xu, R. Acta Pharmacol. Sin. 2003, 24, 97.
[5]	(a) Zhou, F.; Liu, Y.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381. doi: 10.1002/adsc.v352:9
	(b) Klein, J.; Taylor, R. Eur. J. Org. Chem. 2011, 6821.
	(c) Xiao, Y.-L.; Zhou, Y.; Wang, J.; Wang, J.-X.; Liu, H. Chin. J. Org. Chem. 2015, 35, 2035. (in Chinese) doi: 10.6023/cjoc201504045
	(肖永龙, 周宇, 王江, 王进欣, 柳红, 有机化学, 2015, 35, 2035.) doi: 10.6023/cjoc201504045
[6]	(a) Cui, C. B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651. doi: 10.1016/0040-4020(96)00737-5 pmid: 16028899
	(b) Cui, C. B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832. pmid: 16028899
	(c) Ding, K.; Lu, Y.; Nikolovska-Coleska, Z.; Qiu, S.; Ding, Y.; Gao, W.; Stuckey, J.; Krajewski, K.; Roller, P.; Tomita, Y.; Parrish, D.; Deschamps, J.; Wang, S. J. Am. Chem. Soc. 2005, 127, 10130. pmid: 16028899
	(d) Yu, Q.; Guo, P.; Jian, J.; Chen, Y.; Xu, J. Chem. Commun. 2018, 54, 1125. doi: 10.1039/C7CC08938D pmid: 16028899
[7]	Kitamura, H.; Kato, A.; Esaki, T. Eur. J. Pharmacol. 2001, 418, 225. pmid: 11343694
[8]	(a) Abdukader;, A.; Zhang, Y.-H.; Zhang, Z.-P.; Liu, C.-J. Chin. J. Org. Chem. 2016, 36, 875. (in Chinese)
	(阿布力米提·阿布都卡德尔, 张永红, 张增鹏, 刘晨江, 有机化学, 2016, 36, 875.)
	(b) Liu, Y.-J.; Lin, L.-Q.; Han, Y.-H.; Zhang, X. Chin. J. Org. Chem. 2019, 39, 2705. (in Chinese)
	(刘颖杰, 林立青, 韩莹徽, 张鑫, 有机化学, 2019, 39, 2705.) doi: 10.6023/cjoc201904014
	(c) Wang, L.-L.; Zhang, Z.-Y.; Han, H.-B.; Liu, X.-L.; Bu, Z.-W.; Wang, Q.-L. Chin. J. Org. Chem. 2021, 41, 12. (in Chinese) doi: 10.6023/cjoc202007045
	(王乐乐, 张子莹, 韩华彬, 刘雄利, 卜战伟, 王琪琳, 有机化学, 2021, 41, 12.) doi: 10.6023/cjoc202007045
[9]	(a) Xu, S.-M.; Chen, J.-Q.; Liu, D.; Bao, Y.; Liang, Y.-M.; Xu, P.-F. Org. Chem. Front. 2017, 4, 1331. doi: 10.1039/C7QO00012J pmid: 24108594
	(b) Zheng, L.-W.; Huang, H.-L.; Yang, C.; Xia, W.-J. Org. Lett. 2015, 17, 1034. doi: 10.1021/acs.orglett.5b00144 pmid: 24108594
	(c) Li, X.; Xu, X.-S.; Hu, P.-Z.; Xiao, X.-Q.; Zhou, C. J. Org. Chem. 2013, 78, 7343. doi: 10.1021/jo401069d pmid: 24108594
	(d) Shen, T.; Yuan, Y.-Z.; Song, S.; Jiao, N. Chem. Commun. 2014, 50, 4115. doi: 10.1039/c4cc00401a pmid: 24108594
	(e) Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., nt. Ed. 2013, 52, 3972. pmid: 24108594
	(f) Li, Y.-M.; Shen, Y.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991. doi: 10.1016/j.tet.2014.01.065 pmid: 24108594
	(g) Xie, J.; Xu, P.; Li, H.-M.; Xue, Q.-C.; Jin, H.-G.; Cheng, Y.-X.; Zhu, C.-J. Chem. Commun. 2013, 49, 5672. doi: 10.1039/c3cc42672f pmid: 24108594
	(h) Li, Z.; Zhang, Y.; Zhang, L.; Liu, Z.-Q. Org. Lett. 2014, 16, 382. doi: 10.1021/ol4032478 pmid: 24108594
	(i) Li, Y.-H.; Wang, J.-J.; Wei, X.-H.; Yang, S.-D. Chin. J. Org. Chem. 2015, 35, 638. (in Chinese) doi: 10.6023/cjoc201412030 pmid: 24108594
	(李永红, 王君姣, 魏小红, 杨尚东, 有机化学, 2015, 35, 638.) doi: 10.6023/cjoc201412030 pmid: 24108594
	(j) Zhang, J.; Liu, P.; Sun, P.-P. Chin. J. Org. Chem. 2021, 41, 185. (in Chinese) doi: 10.6023/cjoc202006010 pmid: 24108594
	(张杰, 刘平, 孙培培, 有机化学, 2021, 41, 185.) doi: 10.6023/cjoc202006010 pmid: 24108594
	(k) Li, L.; Deng, M.; Zheng, S.-C.; Xiong, Y.-P.; Tan, B.; Liu, X.-Y. Org. Lett. 2014, 16, 504. doi: 10.1021/ol403391v pmid: 24108594
	(l) Xu, P.; Xie, J.; Xue, Q.-C.; Pan, C.-D.; Cheng, Y.-X.; Zhu, C.-J. Chem.-Eur. J. 2013, 19, 14039. doi: 10.1002/chem.201302407 pmid: 24108594
	(m) Tang, X.-J.; Thomoson, C.; Dolbier, W. Org. Lett. 2014, 16, 4594. doi: 10.1021/ol502163f pmid: 24108594
	(n) Wang, J.-Y.; Su, Y.-M.; Yin, F.; Bao, Y.; Zhang, X.; Xu, Y.-M.; Wang, X.-S. Chem. Commun. 2014, 50, 4108. doi: 10.1039/C3CC49315F pmid: 24108594
	(o) Yang, F.; Klumphu, P.; Liang, Y.-M.; Lipshutz, B. H. Chem. Commun. 2014, 50, 936. doi: 10.1039/C3CC48131J pmid: 24108594
	(p) Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128. doi: 10.1021/ol403739w pmid: 24108594
	(q) Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., nt. Ed. 2013, 52, 7985. pmid: 24108594
	(r) Shen, T.; Yuan, Y.-Z.; Jiao, N. Chem. Commun. 2014, 50, 554. doi: 10.1039/C3CC47336H pmid: 24108594
	(s) Chen, J.-R.; Yu, X.-Y.; Xiao, W.-J. Synthesis 2015, 47, 604. doi: 10.1055/s-00000084 pmid: 24108594
[10]	(a) Zhou, M.-B.; Song, R.-J.; Ouyang, X.-H.; Liu, Y.; Wei, W.-T.; Deng, G.-B.; Li, J.-H. Chem. Sci. 2013, 4, 2690. doi: 10.1039/c3sc50810b
	(b) Correia, V. G.; Abreu, J. C.; Barata, C. A. E.; Andrade, L. H. Org. Lett. 2017, 19, 1060. doi: 10.1021/acs.orglett.7b00078
	(c) He, Z.-Y.; Guo, J.-Y.; Tian, S.-K. Adv. Synth. Catal. 2018, 360, 1544. doi: 10.1002/adsc.v360.7
[11]	(a) Jatoi, A. H.; Pawar, G. G.; Robert, F.; Landais, Y. Chem. Commun. 2019, 55, 466. doi: 10.1039/C8CC08326F pmid: 28664204
	(b) Jing, K.; Cui, P.-C.; Wang, G.-W. Chem. Commun. 2019, 15, 12551. pmid: 28664204
	(c) Jouffroy, M.; Kong, J. Chem.-Eur. J. 2019, 25, 2217. doi: 10.1002/chem.201806159 pmid: 28664204
	(d) Pawar, G. G.; Robert, F.; Grau, E.; Cramail, H.; Landais, Y. Chem. Commun. 2018, 54, 9337. doi: 10.1039/C8CC05462B pmid: 28664204
	(e) Bai, Q.-F.; Jin, C.-G.; He, J.-Y.; Feng, G.-F. Org. Lett. 2018, 20, 2172. doi: 10.1021/acs.orglett.8b00449 pmid: 28664204
	(f) Fan, H.-Q.; Pan, P.; Zhang, Y.-Q.; Wang, W. Org. Lett. 2018, 20, 7929. doi: 10.1021/acs.orglett.8b03503 pmid: 28664204
	(g) Petersen, W. F.; Taylor, R. J. K.; Donald, J. R. Org. Lett. 2017, 19, 874. doi: 10.1021/acs.orglett.7b00022 pmid: 28664204
	(h) Petersen, W. F.; Taylor, R. J. K.; Donald, J. R. Org. Biomol. Chem. 2017, 15, 5831. doi: 10.1039/c7ob01274h pmid: 28664204
	(i) Cheng, W.-M.; Shang, R.; Yu, H.-Z.; Fu, Y. Chem.-Eur. J. 2015, 21, 13191. doi: 10.1002/chem.v21.38 pmid: 28664204
	(j) Yuan, M.; Chen, L.; Wang, J.-W.; Chen, S.-J.; Wang, K.-C.; Xue, Y.-B.; Yao, G.-M.; Luo, Z.-W.; Zhang, Y.-G. Org. Lett. 2015, 17, 346. doi: 10.1021/ol503459s pmid: 28664204
[12]	Beck, E.; Grimster, N.; Hatley, R.; Gaunt, M. J. Am. Chem. Soc. 2006, 128, 2528. doi: 10.1021/ja058141u
[13]	(a) Mi, X.; Wang, C.; Huang, M.; Zhang, J.; Wu, Y.; Wu, Y. Org. Lett. 2014, 16, 3356. doi: 10.1021/ol5013839
	(b) Yan, K.; Yang, D.; Wei, W.; Wang, F.; Shuai, Y.; Li, Q.; Wang, H. J. Org. Chem. 2015, 80, 1550. doi: 10.1021/jo502474z
	(c) Liu, T.; Ding, Q.; Zong, Q.; Qiu, G. Org. Chem. Front. 2015, 2, 670. doi: 10.1039/C5QO00029G
[14]	Suárez-Castillo, O. R.; Meléndez-Rodríguez, M.; Castelán-Duarte, L. E.; Sánchez-Zavala, M.; Rivera-Becerril, E.; Morales-Ríos, M. S.; Joseph-Nathan, P. Tetrahedron: Asymmetry 2009, 20, 2374. doi: 10.1016/j.tetasy.2009.09.017

Entry	Catalyst (mol%)	Oxidant (equiv.)	Solvent	Yield^b/%
1	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN	28
2	AgNO₃ (10)	K₂S₂O₈ (2)	H₂O	46
3	AgNO₃ (10)	K₂S₂O₈ (2)	THF	<5
4	AgNO₃ (10)	K₂S₂O₈ (2)	DCM	<5
5	AgNO₃ (10)	K₂S₂O₈ (2)	DMSO	<5
6	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃OH	15
7	AgNO₃ (10)	K₂S₂O₈ (2)	DMF	31
8	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=3∶1)	46
9	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶3)	54
10	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
11	AgOAc (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	64
12	Ag₂O (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
13	Ag₂CO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	76
14	CuBr (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
15	Cu(OAc)₂ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
16	Ag₂CO₃ (10)	Na₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	48
17	Ag₂CO₃ (10)	(NH₄)₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	10
18	Ag₂CO₃ (10)	TBHP (2)	CH₃CN/H₂O (V∶V=1∶1)	nr
19	Ag₂CO₃ (10)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	86
20	Ag₂CO₃ (10)	K₂S₂O₈ (1)	CH₃CN/H₂O (V∶V=1∶1)	72
21	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	85 (82)^c
22^d	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
23^e	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
24^f	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	39
25	—	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	54
26	Ag₂CO₃ (5)	—	CH₃CN/H₂O (V∶V=1∶1)	Trace

Entry	Catalyst (mol%)	Oxidant (equiv.)	Solvent	Yield^b/%
1	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN	28
2	AgNO₃ (10)	K₂S₂O₈ (2)	H₂O	46
3	AgNO₃ (10)	K₂S₂O₈ (2)	THF	<5
4	AgNO₃ (10)	K₂S₂O₈ (2)	DCM	<5
5	AgNO₃ (10)	K₂S₂O₈ (2)	DMSO	<5
6	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃OH	15
7	AgNO₃ (10)	K₂S₂O₈ (2)	DMF	31
8	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=3∶1)	46
9	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶3)	54
10	AgNO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
11	AgOAc (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	64
12	Ag₂O (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	60
13	Ag₂CO₃ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	76
14	CuBr (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
15	Cu(OAc)₂ (10)	K₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	Trace
16	Ag₂CO₃ (10)	Na₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	48
17	Ag₂CO₃ (10)	(NH₄)₂S₂O₈ (2)	CH₃CN/H₂O (V∶V=1∶1)	10
18	Ag₂CO₃ (10)	TBHP (2)	CH₃CN/H₂O (V∶V=1∶1)	nr
19	Ag₂CO₃ (10)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	86
20	Ag₂CO₃ (10)	K₂S₂O₈ (1)	CH₃CN/H₂O (V∶V=1∶1)	72
21	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	85 (82)^c
22^d	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
23^e	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	76
24^f	Ag₂CO₃ (5)	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	39
25	—	K₂S₂O₈ (1.5)	CH₃CN/H₂O (V∶V=1∶1)	54
26	Ag₂CO₃ (5)	—	CH₃CN/H₂O (V∶V=1∶1)	Trace

N-苯基丙烯酰胺与草氨酸衍生物的脱羧氨甲酰化反应研究