Copper-Catalyzed Three-Component Synthesis of Quinolines via Oxidation and Aza-Diels-Alder Reaction

doi:10.6023/cjoc202007003

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 318-324.DOI: 10.6023/cjoc202007003 Previous Articles Next Articles

Article

铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

秦锋^a, 汤琳^a, 黄飞^a, 李晓悦^a, 张武^a^,^*()

a 安徽师范大学化学与材料科学学院安徽芜湖 241000

收稿日期:2020-07-01 修回日期:2020-08-07 发布日期:2020-08-31
通讯作者: 张武
作者简介:
* Corresponding author. E-mail: zhangwu@ahnu.edu.cn
基金资助:
国家自然科学基金(21272006)

Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction

Feng Qin^a, Lin Tang^a, Fei Huang^a, Xiaoyue Li^a, Wu Zhang^a^,^*()

a College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000

Received:2020-07-01 Revised:2020-08-07 Published:2020-08-31
Contact: Wu Zhang
Supported by:
the National Natural Science Foundation of China(21272006)

1. cjoc202007003辅助材料.pdf(2406KB)

Abstract

A tandem three-component reaction for the synthesis of quinolines from anilines, styrene and dimethyl sulfoxide (DMSO) has been developed. Dimethyl sulfoxide (DMSO) served as one-carbon synthon and solvent. The mechanism studies revealed that imine intermediate was involved and inverse electron demand Aza-Diels-Alder reaction was occurred. This method is featured by environmentally benign, good functional group tolerance and good to excellent yield.

Key words: copper-catalyzed, multi-component reaction, quinoline derivatives, Aza-Diels-Alder reaction

Cite this article

Feng Qin, Lin Tang, Fei Huang, Xiaoyue Li, Wu Zhang. Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 318-324.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 21

[1]	(a) Contelles M.; PrezMayoral J.E.; Samadi A.; Carreiras M.C. Chem. Rev. 2009, 109, 2652.
	(b) Sridharan V.; Suryavanshi P.A.; Menndez J.C. Chem. Rev. 2011, 111, 7157.
	(c) Renteria I.B.; Barranco P.G.; Garcia1, A.; Rivera, G.; Banik, K.Curr. Med. Chem. 2012, 19, 4377.
	(d) Hu Y.Q.; Gao C.; Zhang S.; Xu L.; Xu Z.; Feng. L. S.; Wu, X.; Zhao, F.Eur. J. Med. Chem. 2017, 139, 222.
	(e) Andrews S.; Burgess S.J.; Skaalrud D.; Kelly J.X.; Peyton D. J. Med. Chem. 2010, 53, 916.
	(f) Tseng C.H.; Tung C.W.; Peng S.I.; Chen Y.L.; Tzeng C.C.; Cheng C.M. Molecules 2018, 23, 1036.
	(g) Sandhya B.; Suresh K.; Sushma D.; Rajiv K. J. Pharm. Sci. 2010, 2, 64.
	(h) Liberto N.A.; Simoes J.B.; Silva S.D.; Silva C.J.; Modolo L.V.; Fatima A. Bioorg. Med. Chem. 2017, 25, 1154.
[2]	(a) Cohn E.W. J. Am. Chem. Soc. 1939, 52, 3685.
	(b) Gould R.G.; Jacobs W.A. J. Am. Chem. Soc. 1939, 61, 2890.
	(c) Yamashkin S.A.; Oreshkina. E. A.Chem. Heterocycl. Compd. 2006, 42, 701.
[3]	(a) Cho C.S.; Kim B.T.; Kim T.J.; Shim S.C. Chem. Commun. 2001, 2576.
	(b) Heravi M.M.; Asadi S.; Azarakhshi F. Curr. Org. Synth. 2014, 11, 701.
[4]	(a) Eisch J.J.; Dluzniewski T. J. Org. Chem. 1989, 54, 1269.
	(b) Ren L.; Lei T.; Ye J.X.; Gong L.Z. Angew. Chem., Int. Ed. 2012, 51, 771.
	(c) Perez-Mayoral M.; Musilova Z.; Gil B.; Marszalek B.; Polozij M. Dalton Trans. 2012, 41, 4036.
	(d) Reddy B.V.; Venkateswarlu A.; Reddy G.N.; Reddy Y.V. Tetrahedron Lett. 2013, 54, 5767.
[5]	(a) Sloop J.C. J. Phys. Org. Chem. 2009, 22, 110.
	(b) El Kharrat, S.; Laurent, P.; Blancou, H. Tetrahedron 2014, 70, 1252.
	(c) Yuan S.Z.; Zhang K.H.; Xia J.J. Asian. J. Chem. 2013, 8, 5535.
[6]	(a) Ge´raldine M.; Claudia L.; Meryem B.; Guillaume D. Chem. Soc. Rev. 2013, 42, 902.
	(b) Zhao P.; Wu X.; Zhou Y.; Geng X.; Wu Y.D.; Wu A.X. Org. Lett. 2019, 21, 2708.
	(c) Devesh C.; Ankit K.D.; Rakesh K.; Upendra S. Eur. J. Org. Chem. 2019, 2019, 2753.
[7]	(a) Cheng Y.F.; Han X.S.; Ouyang H.C.; Rao Y. Chem. Commun. 2012, 48, 2906.
	(b) Wang R.Z.; Fan H.J.; Zhao W.; Li F. Org. Lett. 2012, 18, 3558.
	(c) Saunthwal R.K.; Patel M.; Verma A.K. J. Org. Chem. 2016, 81, 6563.
	(d) Yao S.; Zhou K.J.; Wang J.B.; Cao H.G.; Yu L.; Wu J.Z.; Qiu P.H.; Xu Q. Green Chem. 2017, 19, 2945.
[8]	Huma H.Z.S.; Halder R.; Kalra S.S.; Das J.; Iqbal J. Tetrahedron Lett. 2002, 43, 6485.
[9]	Kong L.; Yu S.; Zhou X.; Li X. Org. Lett. 2016, 18, 588.
[10]	(a) Xu X.F.; Liu W.M.; Wang Z.Q.; Feng Y.Q.; Yan Y.L.; Zhang X. Tetrahedron Lett. 2016, 57, 226.
	(b) Zhang X.; Xu X.F. Asian J. Chem. 2014, 9, 3089.
[11]	(a) Li C.S.; Li J.X.; An Y.N.; Peng J.W.; Wu W.Q.; Jiang H.F. J. Org. Chem. 2016, 81, 12189.
	(b) Yuan J.; Yu J.T.; Jiang Y.; Cheng J. Org. Biomol. Chem. 2017, 15, 1334.
	(c) Hu K.; Zheng Q.Q.; Gong J.L.; Cheng T.X.; Qi L.J.; Shao Y.L.; Chen J.X. Org. Lett. 2018, 20, 3083.
[12]	(a) Youn S.W.; Yoo H.J.; Lee E.M.; Lee S.Y. Adv. Synth. Catal. 2018, 360, 278.
	(b) Phanindrudu M.; Wakade S.B.; Tiwari D.K.; Likhar P.R.; Tiwari D.K. J. Org. Chem. 2018, 83,9137.
	(c) Jiang T.S.; Wang X.; Zhang X.L. Tetrahedron Lett. 2018, 59, 2979.
[13]	Midya S.P.; Sahoo M.K.; Landge V.; Rajamohanan P.R.; Balaraman E. Nat. Commun. 2015, 6, 8591.
[14]	(a) Mondal R.R.; Khamarui S.; Maiti D.K. ACS Omega 2016, 1, 251.
	(b) Xu X.F.; Yang Y.R.; Chen X.; Zhang X.; Yi W. Org. Biomol. Chem. 2017, 15, 9061.
[15]	(a) Wu X.F.; Natte K. Adv. Synth. Catal. 2016, 358, 336.
	(b) Wu X.; Zhang J.J.; Liu S.; Gao Q.H.; Wu A.X. Adv. Synth. Catal. 2016, 358, 218.
	(c) Wakada S.B.; Tiwari D.K.; Ganesh P.S.K. P.; Phanindrudu, M.; Likhar, P.R.; Tiwari, D.K.Org. Lett. 2017, 19, 4948.
[16]	Xu X.F.; Yang Y.R.; Zhang X.; Yi W. Org. Lett. 2018, 20, 566.
[17]	(a) Jadhav S.D.; Singh A. Org. Lett. 2017, 19, 5673.
	(b) Liu Y.F.; Hu Y.H.; Cao Z.Z.; Zhan X.; Luo W.P.; Liu Q.; Guo C.C. Adv. Synth. Catal. 2018, 360, 2691.
[18]	Cen J.C.; Li J.X.; Zhang Y.; Zhu Z.Z.; Yang S.R.; Jiang H.F. Org. Lett. 2018, 20, 4434.
[19]	Ramesh D.; Shekaraiah D.; Bhahwal A.S. Org. Chem. Front. 2015, 2, 515.
[20]	Liu J.; Liu F.; Zhu Y.Z.; Ma X.G.; Jia X.D. Org. Lett. 2015, 17, 1409.
[21]	(a) Ji X.C.; Huang H.W.; Li Y.B.; Chen H.J.; Jiang H.F. Angew. Chem., Int. Ed. 2012, 51, 7292.
	(b) Wang H.K.; Wang C.; Huang K.M.; Liu L.Y.; Chang W.X.; Li J. Org. Lett. 2016, 18, 2367.

Entry	Catalyst	Oxidant	Solvent	Yield ^b /%
1	CuBr	K ₂S ₂O ₈	DMF	37
2	CuBr	K ₂S ₂O ₈	DMA	23
3	CuBr	K ₂S ₂O ₈	DMSO	67
4	CuBr	K ₂S ₂O ₈	NMP	nr
5	Cu(OAc) ₂	K ₂S ₂O ₈	DMSO	34
6	CuCl ₂	K ₂S ₂O ₈	DMSO	38
7	CuBr ₂	K ₂S ₂O ₈	DMSO	41
8	CuCl	K ₂S ₂O ₈	DMSO	58
9	CuI	K ₂S ₂O ₈	DMSO	76
10	—	K ₂S ₂O ₈	DMSO	Trace
11 ^c	CuI	K ₂S ₂O ₈	DMSO	69
12 ^d	CuI	K ₂S ₂O ₈	DMSO	44
13	CuI	TBHP	DMSO	nr
14	CuI	O ₂	DMSO	nr
15	CuI	(NH ₄) ₂S ₂O ₈	DMSO	36
16	CuI	—	DMSO	nr
17 ^e	CuI	K ₂S ₂O ₈	DMSO	42
18 ^f	CuI	K ₂S ₂O ₈	DMSO	63
19 ^g	CuI	K ₂S ₂O ₈	DMSO	77
20 ^h	CuI	K ₂S ₂O ₈	DMSO	83
21 ⁱ	CuI	K ₂S ₂O ₈	DMSO	<10

Entry	Catalyst	Oxidant	Solvent	Yield ^b /%
1	CuBr	K ₂S ₂O ₈	DMF	37
2	CuBr	K ₂S ₂O ₈	DMA	23
3	CuBr	K ₂S ₂O ₈	DMSO	67
4	CuBr	K ₂S ₂O ₈	NMP	nr
5	Cu(OAc) ₂	K ₂S ₂O ₈	DMSO	34
6	CuCl ₂	K ₂S ₂O ₈	DMSO	38
7	CuBr ₂	K ₂S ₂O ₈	DMSO	41
8	CuCl	K ₂S ₂O ₈	DMSO	58
9	CuI	K ₂S ₂O ₈	DMSO	76
10	—	K ₂S ₂O ₈	DMSO	Trace
11 ^c	CuI	K ₂S ₂O ₈	DMSO	69
12 ^d	CuI	K ₂S ₂O ₈	DMSO	44
13	CuI	TBHP	DMSO	nr
14	CuI	O ₂	DMSO	nr
15	CuI	(NH ₄) ₂S ₂O ₈	DMSO	36
16	CuI	—	DMSO	nr
17 ^e	CuI	K ₂S ₂O ₈	DMSO	42
18 ^f	CuI	K ₂S ₂O ₈	DMSO	63
19 ^g	CuI	K ₂S ₂O ₈	DMSO	77
20 ^h	CuI	K ₂S ₂O ₈	DMSO	83
21 ⁱ	CuI	K ₂S ₂O ₈	DMSO	<10

铜催化氧化和Aza-Diels-Alder反应三组分合成喹啉

Copper-Catalyzed Three-Component Synthesis of Quinolines via
Oxidation and Aza-Diels-Alder Reaction

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 21

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119.
[2]	Chunyang Liu, Yan Li, Qian Zhang. Copper-Catalyzed Allylic C(sp³)—H Sulfonylation of Cyclic Olefins [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1091-1101.
[3]	Yamin Sun, Xiyong Li, Jinwei Yuan, Jialin Yu, Shuainan Liu. CuI-Catalyzed Regioselective Synthesis of 3-Arylcoumarins with Arylamines under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 631-640.
[4]	Mingyang Sun, Kun Xu, Bingbing Guo, Chengchu Zeng. Copper-Catalyzed Vicinal C(sp²)—H Selenylation of Benzoic Acid Derivatives Using Air as Oxidant [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2302-2309.
[5]	Qi Wang, Boran Zhu, Guang Yang, Xiantao Ma, Qing Xu. Selective Synthesis of Unsymmetrical N-Heteroaryl Thioethers byBase-Free Direct Multi-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1193-1199.
[6]	Boshi Han, Zheng Shi, Huihong He, Xinghua Zhang. Study on the Copper-Catalyzed Selective Allylation of Aryl (or Alkyl) Halides [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 695-701.
[7]	Xiang Zhou, Rujian Yu, Jiantao Wang, Xiangwen Liao, Yanshi Xiong. Copper-Catalyzed Remote Sulfonylation of 1-Naphthylamides with Sodium-Sulfinates [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4370-4377.
[8]	Sun Xiaohua, Sun Chuance, Feng Lijun, Kang Congmin. Recent Progress in the Synthesis of Thieno[2,3-d]pyrimidine Compounds via Tandem Cyclization [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2626-2640.
[9]	Peng Mei, Zheng Yangfan, Huang Hao, Ye Jia, Deng Xingguo, He Chunlian. Visible-Light-Induced Cycloaddition Involving N-Propargylanilines with Arylsulfonylhydrazides: Rapid Access to 3-Sulfonated Quinoline Derivatives without Base and Catalyst [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2078-2085.
[10]	Liu Boyu, Xu Xianjun, Huang Liliang, Feng Huangdi. One-Pot Synthesis of Unsymmetrical 1,4-Diaminobutynes by Cu(I)-Catalyzed Cross-Coupling of Propiolic Acid, Secondary Amine, Aldehydes and Formaldehyde [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1290-1296.
[11]	Wang Cai, Zhou Feng, Zhou Jian. Recent Advances in the Enantioselective Copper(I)-Catalyzed Azide-Alkyne Cycloaddition Reaction [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3065-3077.
[12]	Yang Siqi, Li Xin, Peng Zhuojin, Yu Wenyan, Wang Guangxu, Jin Yalan, Zheng Bingbing, Dai Hongxue, Bai Dachang. Synthesis of Pentafluoroethylated Pyridines via Cu-Catalyzed[3+3] Cycloaddition Reaction of Oxime Acetates [J]. Chin. J. Org. Chem., 2019, 39(6): 1623-1629.
[13]	Ren Peixing, Qi Lin, Fang Zhuoyue, Wu Tianshu, Gao Yameng, Shen Song, Song Jinyan, Wang Lijing, Li Wei. Copper-Catalyzed Sulfeno-/Seleno-amination of β,γ-Unsaturated Hydrazones with Disulfides/Diselenides toward Sulfenylated/Selenylated Pyrazolines [J]. Chin. J. Org. Chem., 2019, 39(6): 1776-1786.
[14]	Zhao Xinyu, Ding Yangyang, Lü Yingtao, Kang Congmin. Research Progress on Green Synthesis of Imidazo[1,2-a]pyridine Compounds [J]. Chin. J. Org. Chem., 2019, 39(5): 1304-1315.
[15]	Zhou Anxi, Zhou Xiaofei, Mao Liuliang, Zheng Dagui, Zhu Xianhong, Chen Zongbao. Copper-Catalyzed Oxidative Cross-Coupling Reactions for the Synthesis of β-Acyl-α-amino Acid Derivatives in Aqueous Medium [J]. Chin. J. Org. Chem., 2019, 39(4): 1070-1078.