Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles

doi:10.6023/cjoc201509020

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 520-526.DOI: 10.6023/cjoc201509020 Previous Articles Next Articles

Articles

串联式三组分反应构建取代吡唑杂环

李玉峰, 黄佳维, 顾嘉超, 黄浩, 钮长盛, 马鸿飞

南京工业大学化学与分子工程学院南京 211816

收稿日期:2015-09-18 修回日期:2015-11-12 发布日期:2015-12-07
通讯作者: 李玉峰 E-mail:yufengli@njtech.edu.cn

Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles

Li Yufeng, Huang Jiawei, Gu Jiachao, Huang Hao, Niu Changsheng, Ma Hongfei

College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816

Received:2015-09-18 Revised:2015-11-12 Published:2015-12-07

1. Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles.PDF(3139KB)

Abstract

A sequential three-component reaction for the assembly of functionalized pyrazoles is described. Aldehydes are treated with hydrazines in dichloroethane to generate hydrazones (3), which in situ take place aza-Michael reaction quickly with methyl propiolate (4) catalyzed by CuCl to give Michael adducts (5). Subsequent oxidation of 5 with stoichiometric FeCl₃ provides substituted pyrazoles with high to excellent yields. The intermediates of the synthetic method are not necessary to isolate. Aliphatic hydrazines, aromatic hydrazines as well as aromatic aldehydes are well adaptable to the reaction.

Key words: hydrazine, aldehyde, methyl propiolate, pyrazoles, three-component reaction

Cite this article

Li Yufeng, Huang Jiawei, Gu Jiachao, Huang Hao, Niu Changsheng, Ma Hongfei. Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles[J]. Chin. J. Org. Chem., 2016, 36(3): 520-526.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Abdel-Gawad, M. S.; Abdel-Aziem, A. M.; Ghorab, M. Phosphorus, Sulfur Silicon Relat. Elem. 2003, 178, 1793.
[2] Eriksson, I. B.; Quinlan, J. D. Drugs 2006, 66, 1410.
[3] Farghaly, A. M.; Soliman, G. S. F.; El Semary, A. M. M.; Rostom, F. A. S. Pharmazie 2001, 56, 23.
[4] Seki, K.; Isegawa, J.; Fukuda, M.; Oki, M. Chem. Pharm. Bull. 1984, 32, 1566.
[5] Cottineau, B.; Toto, P.; Marot, C.; Pipaud, A.; Chenault, J. Bioorg. Med. Chem. Lett. 2002, 12, 2102.
[6] Cardia, C. M.; Corda, L.; Fadda, A. M.; Maccioni, A. M.; Maccioni, E.; Plumitallo, A. Farmaco 1998, 53, 696.
[7] Mullican, D. M.; Wilson, W. M.; Cannor, T. D.; Kostlan, R. C.; Dyer, D. R. J. Med. Chem. 1993, 36, 1088.
[8] Rahman, M. A.; Siddiqui, A. A. Int. J. Pharm. Sci. Drug Res. 2010, 2, 165.
[9] Turechek, W. W.; Peres, N. A.; Werner, N. A. Plant Dis. 2006, 90, 862.
[10] James, D. M.; William, D. B. WO 2003055860, 2003 [Chem. Abstr. 2003, 139, 101122].
[11] Okada, I.; Shiga, Y.; Kikutake, K. JP 2002205985, 2002 [Chem. Abstr. 2002, 137, 93748].
[12] Kyomura, N.; Fukuchi, T.; Okui, S. WO 9845274, 1998 [Chem. Abstr. 1998, 129, 302635].
[13] Yamamoto, S.; Satou, T.; Igai, T.; Oguchi, T.; Nawamaki, T. JP 60208977, 1985 [Chem. Abstr. 1985, 104, 148871].
[14] Ma, C. W.; Li, Y. M.; Wen, P.; Yan, R. L.; Ren, Z. Y.; Huang, G. S. Synlett 2011, 1321.
[15] Peruncheralathan, S.; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70, 10030.
[16] Manecke, G.; Schenck, H. U. Tetrahedron Lett. 1969, 8, 617.
[17] Wang, Z. S.; Ye, H. T.; Xiao, D.; Gao, J. S.; Yu, Y. H.; Hou, G. F.; Yan, P. F. Chin. J. Org. Chem. 2014, 34, 2057 (in Chinese). (王子时, 叶汉韬, 肖丹, 马东升, 高金胜, 于颖慧, 侯广峰, 闫鹏飞, 有机化学, 2014, 34, 2057.)
[18] Chen, B.; Yu, C. J.; Zhang, G. Z. Chin. J. Org. Chem. 2015, 35, 625 (in Chinese). (陈斌, 于丛军, 张国柱, 有机化学, 2015, 35, 625.)
[19] Zheng, C. Z.; Xun, X. D.; Wang, Y. Z.; Zhao, D. J.; Zhang, J. Z. Chin. J. Org. Chem. 2015, 35, 1137 (in Chinese). (郑纯智, 徐小丹, 王雅珍, 赵德建, 张继振. 有机化学, 2015, 35, 1137.)
[20] Ma, C.; Li, Y; Wen, P.; Yan, R.; Ren, Z; Huang, G. Synlett 2011, 1321.
[21] Yavri, I.; Khalili, G.; Mirzaei, A. Helv. Chim. Acta 2010, 93, 277.
[22] Safaei, S.; Mohammadpoor-Baltork, I.; Khosropour, A. R.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V. Adv. Synth. Catal. 2012, 354, 3095.
[23] Ji, X. C.; Huang, H. W.; Wu, W. Q.; Li, X. W.; Jiang, H. F. J. Org. Chem. 2013, 78, 11155.
[24] Li, Y. F.; Shi, J.; Wu, Z.; Wang, X. L.; Wu, X.; Gu, J.; Bu, H.; Ma, H. Tetrahedron 2014, 70, 2472.
[25] Li, Y. F.; Wu, Z.; Shi, J.; Pan, Y.; Bu, H. Z.; Ma, H.; Gu, J.; Huang, H.; Wang, Y.; Wu, L. Tetrahedron 2014, 70, 8971.
[26] Li, Y. F.; Wu, Z.; Shi, J.; Bu, H.; Gu, J. C.; Pan, Y. Tetrahedron 2014, 70, 3134.
[27] Zhang, L. Z.; Li, L. Q.; Ren, X. J.; Xie, Z. X. Acta Chim. Sinica 2008, 66, 589 (in Chinese). (张鲁中, 李立奇, 任小娟, 谢志翔, 化学学报, 2008, 66, 589.)
[28] Li, R. S.; Wang, S. R.; Lu, W. J. Org. Lett. 2007, 11, 2219.
[29] Yang, L.; Lei, C. H.; Wang, D. X.; Huang, Z. T.; Wang, M. X. Org. Lett. 2010, 17, 3918.

串联式三组分反应构建取代吡唑杂环

Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[2]	Wenqian Wu, Chunxia Chen, Jinsong Peng, Zhanyu Li. Research Progress of Carbonyl α-Position Amination [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2743-2763.
[3]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[4]	Yuliang Chen, Fengkai He, Siyun Wang, Dingcheng Jia, Yaqun Liu, Yiyong Huang. Kinetic Resolution of Aldehydes Bearing an All-Carbon Quaternary Stereocenter at the α-Position by the Antilla Allylboration [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4294-4302.
[5]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[6]	Haojie Ma, Fengyuan Zhou, Jinlei Liu, Bo Han, Hua Yang, Yuqi Zhang, Jijiang Wang. Construction of Substituted N-Phenylpyrazoles via a Catalyst- Free and Additive-Free Intermolecular Cyclization Process [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1843-1848.
[7]	Huijie Qiao, Liting Yang, Ya Chen, Jialin Wang, Wuxuan Sun, Haobo Dong, Yunwei Wang. An Efficient Three-Component Tandem Approach for the Synthesis of Imidazoheterocycle-Hydrazine Derivatives under Mild Conditions [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1188-1197.
[8]	Huixu Lu, Yonghe Tang, Hongmei Zhou, Weiying Lin. Synthesis and Study of Performance for An Enhanced Formaldehyde Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1163-1169.
[9]	Haorui Wang, Mengchun Ye. Research Advance on Enantioselective Transition Metal-Catalyzed Hydroacylation Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3152-3166.
[10]	Zhenli Xu, Zongxue Zhang, Chenxiang Meng, Xiaoya Zhang, Kai Xu, Lantao Liu, Tao Wang, Haiyun Xu, Guoliang Mao. Ligand-Free Pd-Catalyzed Hydrophosphorylation of Internal Alkynes for the Synthesis of E-Vinylphosphonates [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3264-3271.
[11]	Wenxin Zhao, Mengjun Huang, Shengnan Li, Yujing Liu, Zhongqiu Liu, An'guo Ying. One-Pot Synthesis of 3,4-Dihydropyrimidine-2-one Derivatives via Biginelli Reactions Catalyzed by SnCl₂@MNPs [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2743-2749.
[12]	Chengfei Li, Bo Cen, Wengui Duan, Guishan Lin, Xiu Wang, Baoyu Li. Synthesis, Herbicidal Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-Methyl- 1,2,4-triazole-thioether Compounds Containing Natural Styrene Structure [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2485-2495.
[13]	Yu Zhao, Yang Liu, Xinxin Wang, Yingying Hong, Yingxiu Man, Jinjun Wang, Jiazhu Li. Efficient Synthesis of 3,6-Dialkylcarbazole-1-formaldehyde and 3,6-Dialkylcarbazole-1,8-diformaldehyde [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2435-2444.
[14]	Qian Li, Li Yang, Wei Liu, Tianyun Wang, Yuejie Zhu, Zhengyin Du. Formylation of Phenols and Paraformaldehyde Catalyzed by Ammonium Acetate [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2038-2044.
[15]	Xiang Wang, Ping Chen, Sanjun Zhi, Huayou Hu, Yuhe Kan, Guodong Tang, Zaichao Zhang. Synthesis of 3-Benzo[d]imidazol-2(3H)-ylidene Substituted Pyrano-[3,2-c]chromen-2-ones via Three-Component Reaction [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1241-1245.