Catalytic Synthesis of Pyrazine and Ketone Derivatives by Unsymmetrical Triazolyl-Naphthyridinyl-Pyridine Copper

doi:10.6023/cjoc202107018

Abstract

A novel method for the synthesis of pyrazine and ketone derivatives was developed by using asymmetric ligand-based catalyst TNP-Cu@rGO. The screening of reaction bases, solvents, reaction temperatures and time was conducted to determine optimal reaction conditions. The reaction scope and generality of this methodology for the synthesis of pyrazines were tested and the results showed that this catalytic system had good functional tolerance. More than twenty substrates experiments were successfully set up, and pyrazines with moderate to high yields were isolated. Additionally, this catalytic system could also be used to the systhesis of ketones in good yields. Furthermore, the mechanism investigations were conducted for the synthesis of pyrazine derivatives to better understand the synthesis of pyrazines. The recycling test of TNP-Cu@rGO for the synthesis of pyrazines was investigated and the experiments showed that the catalyst could still maintain high catalytic activity for five times.

Key words: borrowing hydrogen, unsymmetrical, pyrazine, copper

Cite this article

Jiahao Li, Yike Yang, Wenkang Hu, Xiaofeng Xia, Dawei Wang. Catalytic Synthesis of Pyrazine and Ketone Derivatives by Unsymmetrical Triazolyl-Naphthyridinyl-Pyridine Copper[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 190-199.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 9

References 14

[1]	(a) Cai, L.; Zhang, K.; Chen, S.; Lepage, R. J.; Houk, K. N.; Krenske, E. H.; Kwon, O. J. Am. Chem. Soc. 2019, 141, 9537. doi: 10.1021/jacs.9b04803
	(b) Ding, B.; Jiang, Y.; Zhang, Y.; Ye, R.; Sun, J.; Yan, C. Chin. J. Org. Chem. 2020, 40, 1003. (in Chinese) doi: 10.6023/cjoc201910016
	(丁邦东, 姜业朝, 张瑜, 叶蓉, 孙晶, 颜朝国, 有机化学, 2020, 40, 1003.) doi: 10.6023/cjoc201910016
	(c) Wen, D.; Zheng, Q.; Wang, C.; Tu, T. Org. Lett. 2021, 23, 3718. doi: 10.1021/acs.orglett.1c01106
	(d) Zhou, Y.; Zhao, Z.; Zeng, L.; Li, M.; He, Y.; Gu, L. Chin. J. Org. Chem. 2021, 41, 1072. (in Chinese) doi: 10.6023/cjoc202007049
	(周娅琴, 赵志恒, 曾亮, 李鸣, 何永辉, 谷利军, 有机化学, 2021, 41, 1072.) doi: 10.6023/cjoc202007049
	(e) Xie, R.; Lu, G.-P.; Jiang, H.-F.; Zhang, M. J. Catal. 2020, 383, 239. doi: 10.1016/j.jcat.2020.01.034
	(d) Liu, Y.; Meng, J.; Li, C.; Lin, L.; Xu, Y. Chin. J. Org. Chem. 2020, 40, 2742. (in Chinese) doi: 10.6023/cjoc202003056
	(刘颖杰, 孟建萍, 李晨, 林立青, 许颖, 有机化学, 2021, 40, 2742.)
[2]	(a) Yu, H.; Zhang, R.; Yang, F.; Xie, Y.; Guo, Y.; Yao, W.; Zhou, W. Trends Food Sci. Technol. 2021, 112, 795. doi: 10.1016/j.tifs.2021.04.028
	(b) Chen, J.; Wang, Y.; Yu, J.; Cheng, J.; Zheng, H. Chin. J. Org. Chem. 2020, 40, 78. (in Chinese)
	(陈晶晶, 王莹淑, 余珺, 成佳佳, 郑辉东, 有机化学, 2020, 40, 78.) doi: 10.6023/cjoc201908001
	(c) Wang, F.; Wei, M.; Duan, X.; Liu, X.; Yao, S.; Wang, J.; Zhu, H.; Chen, C.; Gu, L.; Zhang, Y. Org. Chem. Front. 2020, 7, 3616. doi: 10.1039/D0QO01030H
	(d) Zhang, H. J.; Yang, Z. P.; Gu, Q.; You, S. L. Org. Lett. 2019, 21, 3314. doi: 10.1021/acs.orglett.9b01060
[3]	(a) Hassan, N. W.; Saudi, M. N.; Abdel-Ghany, Y. S.; Ismail, A.; Elzahhar, P. A.; Sriram, D.; Nassra, R.; Abdel-Aziz, M. M. Bioorg. Chem. 2020, 96, 103610. doi: 10.1016/j.bioorg.2020.103610
	(b) Kučerová-Chlupáčová, M.; Opletalová, V.; Jampílek, J.; Doležel, J.; Dohnal, J.; Pour, M.; Kuneš, J.; Voříšek, V. Collect. Czech. Chem. C 2008, 73, 1. doi: 10.1135/cccc20080001
	(c) Wang, N.; Mani, A.; Chen, X.; Wang, B.; Chen, S.; Yao, C.; Wang, Z. Chin. J. Org. Chem. 2019, 39, 2771. (in Chinese) doi: 10.6023/cjoc201904061
	(王能, Arulkumar, Mani, 陈孝云, 王柏文, 陈思鸿, 姚辰, 汪朝阳, 有机化学, 2019, 39, 2771.) doi: 10.6023/cjoc201904061
	(d) Liu, J.; Xie, Y.; Yang, Q.; Huang, N.; Wang, L. Chin. J. Org. Chem. 2021, 41, 2374. (in Chinese) doi: 10.6023/cjoc202012040
	(刘金妮, 谢益碧, 阳青青, 黄年玉, 王龙, 有机化学, 2021, 41, 2374.) doi: 10.6023/cjoc202012040
	(e) Tian, A.-Q.; Luo, X.-H.; Ren, Z.-L.; Zhao, J.; Wang, L. New J. Chem. 2021, 45, 9614. doi: 10.1039/D1NJ00861G
	(f) Yu, S.-Q.; Liu, N.; Liu, M.-G.; Wang, L. J. Chem. Res. 2021, 45, 237. doi: 10.1177/1747519820966985
[4]	(a) Wei, R.; Bao, H. Chin. J. Org. Chem. 2020, 40, 1797. (in Chinese) doi: 10.6023/cjoc202000034
	(韦榕标, 鲍红丽, 有机化学, 2020, 40, 1797.) doi: 10.6023/cjoc202000034
	(b) Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Chem. Eur. J. 2006, 12, 5142. doi: 10.1002/(ISSN)1521-3765
	(c) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054. doi: 10.1021/ja964391m
	(d) Mizuta, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2005, 70, 2195. doi: 10.1021/jo0481708
	(4e) Vernin, G.; Hornwood, M. P.-E. Chichester 1982, 305, 70.
[5]	(a) Hao, S.; Yang, J.; Liu, P.; Xu, J.; Yang, C.; Li, F. Org. Lett. 2021, 23. 2553. doi: 10.1021/acs.orglett.1c00475
	(b) Liu, P.; Yang, J.; Ai, Y.; Hao, S.; Chen, X.; Li, F. J. Catal. 2021, 396, 281. doi: 10.1016/j.jcat.2021.02.030
	(c) Wei, D.; Yang, P.; Yu, C.; Zhao, F.; Wang, Y.; Peng, Z. J. Org. Chem. 2021, 86, 2254. doi: 10.1021/acs.joc.0c02407
	(d) Meng, C.; Liu, P.; Tung, N. T.; Han, X.; Li, F. J. Org. Chem. 2020, 85, 5815. doi: 10.1021/acs.joc.9b03411
	(e) Zhu, Z.-H.; Li, Y.; Wang, Y.-B.; Lan, Z.-G.; Zhu, X.; Hao, X.-Q. Organometallics 2019, 38, 2156. doi: 10.1021/acs.organomet.9b00146
[6]	(a) Li, F.; Xie, J.; Shan, H.; Sun, C.; Chen, L. RSC Adv. 2012, 2, 8645. doi: 10.1039/c2ra21487c pmid: 29039671
	(b) Liang, R.; Li, S.; Wang, R.; Lu, L.; Li, F. Org. Lett. 2017, 19, 5790. doi: 10.1021/acs.orglett.7b02723 pmid: 29039671
	(c) Fujita, K.-I.; Toyooka, G.; Tuji, A. Synthesis 2018, 50, 4617. doi: 10.1055/s-0037-1610252 pmid: 29039671
	(d) Nallagangula, M.; Sujatha, C.; Bhat, V. T.; Namitharan, K. Chem. Commun. 2019, 55, 8490. doi: 10.1039/C9CC04120F pmid: 29039671
	(e) Sankar, V.; Kathiresan, M.; Sivakumar, B.; Mannathan, S. Adv. Synth. Catal. 2020, 362, 4409. doi: 10.1002/adsc.v362.20 pmid: 29039671
[7]	(a) Cao, L.; Zhao, H.; Tan, Z.; Guan, R.; Jiang, H.; Zhang, M. Org. Lett. 2020, 22, 4781. doi: 10.1021/acs.orglett.0c01580
	(b) Tan, Z.; Ci, C.; Yang, J.; Wu, Y.; Cao, L.; Jiang, H.; Zhang, M. ACS Catal. 2020, 10, 5243. doi: 10.1021/acscatal.0c00394
	(c) Xie, F.; Li, Y.; Chen, X.; Chen, L.; Zhu, Z.; Li, B.; Huang, Y.; Zhang, K.; Zhang, M. Chem. Commun. 2020, 56, 5997. doi: 10.1039/C9CC09649C
	(d) Wu, D.; Cheng, X.; Liu, Y.; Cheng, G.; Guan, X.; Deng, Q. Chin. J. Org. Chem. 2020, 40, 3362. (in Chinese) doi: 10.6023/cjoc202005090
	(吴敦奇, 成轩, 刘炎开, 成果, 管笑宇, 邓清海, 有机化学, 2020, 40, 3362.) doi: 10.6023/cjoc202005090
	(e) Zhang, G.; Jiang, Y.; Ding, C.; Hou, X. Chin. J. Org. Chem. 2020, 40, 3399. (in Chinese) doi: 10.6023/cjoc202006007
	(张高鹏, 江阳杰, 丁昌华, 侯雪龙, 有机化学, 2020, 40, 3399.) doi: 10.6023/cjoc202006007
	(f) Cao, Z.; Qiao, H.; Zeng, F. Organometallics 2019, 38, 797. doi: 10.1021/acs.organomet.8b00791
	(g) Li, S.; Li, X.; Li, Q.; Yuan, Q.; Shi, X.; Xu, Q. Green Chem. 2015, 17, 3260. doi: 10.1039/C4GC02542C
[8]	(a) Balamurugan, G.; Ramesh, R.; Malecki, J. G. J. Org. Chem. 2020, 85, 7125. doi: 10.1021/acs.joc.0c00530
	(b) Liu, Z.; Zhang, X.; Zhang, H.; Jiang, H.; Zhao, X.; Shi, L.; Zhu, X.; Hao, X.; Song, M. Chin. J. Org. Chem. 2020, 40, 2755. (in Chinese) doi: 10.6023/cjoc202003068
	(刘子琳, 张小洁, 张恒, 姜辉, 赵雪梅, 石林林, 朱新举, 郝新奇, 宋毛平, 有机化学, 2020, 40, 2755.) doi: 10.6023/cjoc202003068
	(c) Xie, F.; Li, Y.; Chen, X.; Chen, L.; Zhu, Z.; Li, B.; Huang, Y.; Zhang, K.; Zhang, M. Chem. Commun. 2020, 56, 5997. doi: 10.1039/C9CC09649C
[9]	(a) Yao, W.; Zhang, Y.; Zhu, H.; Ge, C.; Wang, D. Chin. Chem. Lett. 2020, 31, 701. doi: 10.1016/j.cclet.2019.08.049
	(b) Cao, F.; Duan, Z.-C.; Zhu, H.; Wang, D. Mol. Catal. 2021, 503, 111391.
	(c) Xu, Z.; Yu, X.; Sang, X.; Wang, D. Green Chem. 2018, 20, 2571. doi: 10.1039/C8GC00557E
	(d) Yang, Q.; Zhang, Y.; Zeng, W.; Duan, Z.-C.; Sang, X.; Wang, D. Green Chem. 2019, 21, 5683. doi: 10.1039/C9GC02409C
[10]	(a) Tao, R.; Yang, Y.; Zhu, H.; Hu, X.; Wang, D. Green Chem. 2020, 22, 8452. doi: 10.1039/D0GC02341H
	(b) Zhu, G.; Duan, Z.-C.; Zhu, H.; Qi, M.; Wang, D. Mol. Catal. 2021, 505, 111516.
	(c) Zhu, G.; Duan, Z.-C.; Zhu, H.; Ye, D.; Wang, D. Chin. Chem. Lett. 2021, 32, 10.1016/j.cclet.2021.06.060.
	(d) Hu, X.; Yang, B.; Yao, W.; Wang, D. Chin. J. Org. Chem. 2018, 38, 3296. (in Chinese) doi: 10.6023/cjoc201805019
	(胡昕宇, 杨伯斌, 姚玮, 王大伟, 有机化学, 2018, 38, 3296.) doi: 10.6023/cjoc201805019
[11]	Hu, W.; Zhang, Y.; Zhu, H.; Ye, D.; Wang, D. Green. Chem. 2019, 21, 5345. doi: 10.1039/C9GC02086A
[12]	Yang, F.-L.; Wang, Y.-H.; Ni, Y.-F.; Gao, X.; Song, B.; Zhu, X.; Hao, X.-Q. Eur. J. Org. Chem. 2017, 2017, 3481.
[13]	(a) Donthiri, R. R.; Pappula, V.; Mohan, D. C.; Gaywala, H. H.; Adimurthy, S. J. Org. Chem. 2013, 78, 6775. doi: 10.1021/jo400834h
	(b) Li, S.; Li, X.; Li, Q.; Yuan, Q.; Shi, X.; Xu, Q. Green Chem. 2015, 17, 3260. doi: 10.1039/C4GC02542C
	(c) Walsh, K.; Sneddon, H. F.; Moody, C. J. ChemSusChem 2013, 6, 1455. doi: 10.1002/cssc.201300239
	(e) Duron, S. G.; Lindstrom, A.; Bonnefous, C.; Zhang, H.; Chen, X.; Symons, K. T.; Sablad, M.; Rozenkrants, N.; Zhang, Y.; Wang, L.; Yazdani, N.; Shiau, A. K.; Noble, S. A.; Rix, P.; Rao, T. S.; Hassig, C. A.; Smith, N. D. Bioorg. Med. Chem. Lett. 2012, 22, 1237. doi: 10.1016/j.bmcl.2011.11.073
[14]	(a) Cao, X. N.; Wan, X. M.; Yang, F. L.; Li, K.; Hao, X. Q.; Shao, T.; Zhu, X.; Song, M. P. J. Org. Chem. 2018, 83, 3657. doi: 10.1021/acs.joc.8b00013
	(b) Liu, P.; Liang, R.; Lu, L.; Yu, Z.; Li, F. J. Org. Chem. 2017, 82, 1943. doi: 10.1021/acs.joc.6b02758

Entry	Base	Solvent	Temp./℃	Yield^b/%
1	K₂CO₃	Xylene	140	24
2	Na₂CO₃	Xylene	140	Trace
3	K₃PO₄	Xylene	140	33
4	Cs₂CO₃	Xylene	140	97
5	KO^tBu	Xylene	140	95
6	NaO^tBu	Xylene	140	91
7	KOH	Xylene	140	89
8	NaOH	Xylene	140	86
9	CsOH•H₂O	Xylene	140	75
10	Cs₂CO₃	Toluene	140	79
11	Cs₂CO₃	1,4-Dioxane	140	30
12	Cs₂CO₃	DMF	140	61
13	Cs₂CO₃	DMA	140	Trace
14	Cs₂CO₃	1,2-Ethanediol	140	Trace
15	Cs₂CO₃	Xylene	120	76
16	Cs₂CO₃	Xylene	150	97
17	Cs₂CO₃	Xylene	140	85 ^c
18	Cs₂CO₃	Xylene	140	97 ^d
19	Cs₂CO₃	Xylene	140	Trace^e

Entry	Base	Solvent	Temp./℃	Yield^b/%
1	K₂CO₃	Xylene	140	24
2	Na₂CO₃	Xylene	140	Trace
3	K₃PO₄	Xylene	140	33
4	Cs₂CO₃	Xylene	140	97
5	KO^tBu	Xylene	140	95
6	NaO^tBu	Xylene	140	91
7	KOH	Xylene	140	89
8	NaOH	Xylene	140	86
9	CsOH•H₂O	Xylene	140	75
10	Cs₂CO₃	Toluene	140	79
11	Cs₂CO₃	1,4-Dioxane	140	30
12	Cs₂CO₃	DMF	140	61
13	Cs₂CO₃	DMA	140	Trace
14	Cs₂CO₃	1,2-Ethanediol	140	Trace
15	Cs₂CO₃	Xylene	120	76
16	Cs₂CO₃	Xylene	150	97
17	Cs₂CO₃	Xylene	140	85 ^c
18	Cs₂CO₃	Xylene	140	97 ^d
19	Cs₂CO₃	Xylene	140	Trace^e

[1]	Xiao Song, Jing Qing, Jun Li, Xuelei Jia, Fusong Wu, Junrong Huang, Jian Jin, Hengzhi You. Copper-Catalyzed Asymmetric Allyl Alkylation Using Grignard Reagents under Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3174-3179.
[2]	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.
[3]	Zhicheng Bao, Muyao Li, Jianbo Wang. Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1808-1814.
[4]	Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498.
[5]	Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.
[6]	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.
[7]	Biao Han, Weishuang Li, Shuhan Chen, Zelang Zhang, Xue Zhao, Yaoyao Zhang, Lei Zhu. Recent Advances in Copper-Catalyzed Silyl Addition of Unsaturated Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 555-572.
[8]	Li Xu, Lanlan Lü, Xiangshan Wang. Copper-Catalyzed Synthesis of β-Keto Sulfones from Enol Silyl Ether and Sodium Arylsulfinates [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3644-3651.
[9]	Zhiyuan Chen, Mengwei Yang, Jianlin Xu, Yunhe Xu. Regioselective Synthesis of β-Silyl-Substituted Vinylphosphine Oxides via Copper-Catalyzed Protosilylation of Dialkynylphosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3598-3607.
[10]	Xuefeng Jia, Xiangjuan Tong. Recent Progress on Chan-Lam Coupling Reactions Catalyzed by Copper(II) Complexes [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2640-2658.
[11]	Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO₂ at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480.
[12]	Hui Li, Liang Yin. Research Progress of Copper-Catalyzed Direct Vinylogous Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1573-1585.
[13]	Tianyi Sun, Yifan Zhang, Yuanjie Meng, Yi Wang, Qifeng Zhu, Yuxin Jiang, Shihui Liu. Photoredox-Copper Dual-Catalyzed Site-Selective O-Alkylation of Glycosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1414-1422.
[14]	Yiping Wen, Zhengfeng Xie, Tianzhu Shi, Yicheng Chu, Ronggui Zhou, Yishan Tao, Huanmin Liang, Haiyan Qiu, Yunhui Zhao. Synthesis of Triazole Functionalized Triphenylamine Cu²⁺ Fluorescent Probe and Its Application in Detection and HeLa Cells [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1463-1473.
[15]	Jing Shi, Pengfei Guo, Wei Li, Haijing Sun, Lingwu Meng, Xinli Tong. Copper(I)-Catalyzed Aerobic Oxidative Condensation of Biomass-Based Platform Compound Furfurals with Straight-Chain Alcohols [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 905-909.

基于非对称性三唑萘啶吡啶铜催化合成吡嗪与酮衍生物