Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines

doi:10.1007/s40242-016-5495-x

高等学校化学研究 ›› 2016, Vol. 32 ›› Issue (3): 385-389.doi: 10.1007/s40242-016-5495-x

Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines

JANG Hochol^1,2, LIU Wei¹, ZHANG SEAN Xiao'an¹, LIAO Weiwei¹

1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. Department of Chemistry, Kim Il Sung University, Pyongyang, D. P. R. Korea

收稿日期:2015-12-20 修回日期:2016-01-18 出版日期:2016-06-01 发布日期:2016-03-28
通讯作者: SEAN Xiao'an, LIAO Weiwei E-mail:seanzhang@jlu.edu.cn;wliao@jlu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No. 21372096).

Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines

JANG Hochol^1,2, LIU Wei¹, ZHANG SEAN Xiao'an¹, LIAO Weiwei¹

1. Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. Department of Chemistry, Kim Il Sung University, Pyongyang, D. P. R. Korea

Received:2015-12-20 Revised:2016-01-18 Online:2016-06-01 Published:2016-03-28
Contact: SEAN Xiao'an, LIAO Weiwei E-mail:seanzhang@jlu.edu.cn;wliao@jlu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No. 21372096).

摘要/Abstract

摘要：

Phosphine-catalyzed [4+2] annulations of 2-(acetoxymethyl)buta-2,3-dienoates with α-aminonitriles have been developed, in which α-aminonitriles serve as C, N-bisnucleophilic reaction partners and 2-(acetoxymethyl)buta- 2,3-dienoates as "C4 synthons" respectively. A number of α-aminonitriles could be successfully applied to giving multifunctional desired products using PPh₃ as catalyst. This method provides a facile entry to access polysubstituted tetrahydropyridines bearing quaternary carbon centers. The possible reaction mechanism was also proposed.

关键词: Annulation, Catalysis, Tetrahydropyridine

Abstract:

Key words: Annulation, Catalysis, Tetrahydropyridine

JANG Hochol, LIU Wei, ZHANG SEAN Xiao'an, LIAO Weiwei. Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines[J]. 高等学校化学研究, 2016, 32(3): 385-389.

参考文献

[1] Benito A., Pedro A., Cristina A., Curr.Opin.Drug Discovery Dev., 2010, 13(6), 685
[2] Wimone R., Currie K. S., Mitchell S. A., Darrow J. W., Pippin D. A., Comb Chem.High Throughput Screen, 2004, 7, 473
[3] Leeson P. D., Springthorpe B., Nat.Rev.Drug.Discov., 2007, 6, 881
[4] Daly J. W., Spande T. F., Garraffo H. M., J.Nat.Prod., 2005, 68(10), 1556
[5] Michael J. P., Nat.Prod.Rep., 2008, 25, 139
[6] Michael J. P.,The Alkaloids, Academic Press, San Diego, 2001, 55
[7] Comins D. L., Joseph S. P., Advances in Nitrogen Heterocycles, JAI. Press, Greenwich, CT, 1996, 251
[8] Rowland G. B., Rowland E. B., Zhang Q., Antilla J. C., Curr.Org.Chem., 2006, 10(9) , 981
[9] Kouznetsov V. V., Tetrahedron, 2009, 65, 2721
[10] Girling P. R., Kiyoi T., Whiting A., Org.Biomol.Chem., 2011, 9, 3105
[11] Memeo M. G., Quadrelli P., Chem.Eur.J., 2012, 18(40), 12554
[12] Masson G., Lalli C., Benohoud M., Dagousset G., Chem.Soc.Rev., 2013, 42, 902
[13] Lu X., Zhang C., Xu Z., Acc.Chem.Res., 2001, 34, 535
[14] Methot J. L., Roush W. R., Adv.Synth.Catal., 2004, 346, 1035
[15] Lu X., Du Y., Lu C., Pure Appl.Chem., 2005, 77, 1985
[16] Cowen B. J., Miller S. J., Chem.Soc.Rev., 2009, 38, 3102
[17] Ye L. W., Zhou J., Tang Y., Chem.Soc.Rev., 2008, 37, 1140
[18] Denmark S. E., Beutner G. L., Angew.Chem.Int.Ed., 2008, 47, 1560
[19] Wei Y., Shi M., Acc.Chem.Res., 2010, 43, 1005
[20] Zhao Q. Y., Lian Z., Wei Y., Shi M., Chem.Commun., 2012, 48, 1724
[21] Wang Z., Xu X., Kwon O., Chem.Soc.Rev., 2014, 43, 2927
[22] Xu Z., Lu X., Tetrahedron.Lett., 1997, 38(19), 3461
[23] Xu Z., Lu X., J.Org.Chem., 1998, 63, 5031
[24] Zhu X. F., Lan J., Kwon O., J.Am.Chem.Soc., 2003, 125, 4716
[25] Guo H., Xu Q., Kwon O., J.Am.Chem.Soc., 2009, 131, 6318
[26] Chen X. Y., Ye S., Eur.J.Org.Chem., 2012, 5723
[27] Wurz R. P., Fu G. C., J.Am.Chem.Soc., 2005, 127, 12234
[28] Xiao H., Chai Z., Wang H. F., Wang X. W., Cao D. D., Liu W., Lu Y. P., Yang Y. Q., Zhao G., Chem.Eur.J., 2011, 17, 10562
[29] Zhang Q., Yang L., Tong X., J.Am.Chem.Soc., 2010, 132, 2550
[30] Hu P., Hu J., Jiao J., Tong X., Angew.Chem.Int.Ed., 2013, 52, 5319
[31] Albright J. D., Tetrahedron, 1983, 39, 3207
[32] Enders D., Shilvock J. P., Chem.Soc.Rev., 2000, 29, 359
[33] Opatz T., Synthesis, 2009, 12, 1941
[34] Meyer N., Werner F., Opatz T., Synthesis, 2005,6, 945
[35] Bergner I., Opatz T., Synthesis, 2007, 6, 918
[36] Pan F., Chen J. M., Zhuang Z., Fang Y. Z., Zhang S. X. A., Liao W. W., Org.Biomol.Chem., 2012, 10, 2214
[37] Pan F., Chen J. M., Qin T. Y., Zhang S. X. A., Liao W. W., Eur.J.Org.Chem., 2012, 5324
[38] En D., Zou G. F., Guo Y., Liao W. W., J.Org.Chem., 2014, 79, 4456
[39] Zhuang Z., Pan F., Fu J. G., Chen J. M., Liao W. W., Org.Lett., 2011, 13, 6164
[40] Chen J. M., Fang Y. Z., Wei Z. L., Liao W. W., Synthesis, 2012, 44, 1849
[41] Qin T. Y., Liao W. W., Zhang Y. J., Zhang S. X. A., Org.Biomol.Chem., 2013, 11, 984
[42] Chen J. M., Zou G. F., Liao W. W., Angew.Chem.Int.Ed., 2013, 52, 9296

Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines

Phosphine-catalyzed [4+2] Annulations of α-Aminonitriles with Allenoates: Synthesis of Functionalized Tetrahydropyridines

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	FAN Kui, SUN Yining, XU Pengcheng, GUO Jian, LI Zhenhua, SHAO Mingfei. Single-atom Catalysts Based on Layered Double Hydroxides[J]. 高等学校化学研究, 2022, 38(5): 1185-1196.
[2]	MA Chunrong, SONG Bingyi, MA Zhentao, WANG Xiaoqian, TIAN Lin, ZHANG Haoran, CHEN Cai, ZHENG Xusheng, YANG Li-ming, WU Yuen. A Supported Palladium on Gallium-based Liquid Metal Catalyst for Enhanced Oxygen Reduction Reaction[J]. 高等学校化学研究, 2022, 38(5): 1219-1225.
[3]	SONG Jingting, LIU Jia, LOH Kian Ping, CHEN Zhongxin. Ultrahigh Loading Copper Single Atom Catalyst for Palladium-free Wacker Oxidation[J]. 高等学校化学研究, 2022, 38(5): 1239-1242.
[4]	SHU Chengyong, GAN Zhuofan, ZHOU Jia, WANG Zhen, TANG Wei. Highly Efficient Oxygen Reduction Reaction Fe-N-C Cathode in Long-durable Direct Glycol Fuel Cells[J]. 高等学校化学研究, 2022, 38(5): 1268-1274.
[5]	SONG Weiyu, LV Xintong, GAO Yang, WANG Lu. Photocatalytic HER Performance of TiO₂-supported Single Atom Catalyst Based on Electronic Regulation:A DFT Study[J]. 高等学校化学研究, 2022, 38(4): 1025-1031.
[6]	WEI Xiao, LI Xinhao, WANG Kaixue and CHEN Jiesheng. Design of Functional Carbon Composite Materials for Energy Conversion and Storage[J]. 高等学校化学研究, 2022, 38(3): 677-687.
[7]	DU Shihao, BIAN Xuanang, ZHAO Yunxuan, SHI Run, and ZHANG Tierui. Progress and Prospect of Photothermal Catalysis[J]. 高等学校化学研究, 2022, 38(3): 723-734.
[8]	HAO Zhimin, LIU Dapeng, GE Huaiyun, ZUO Xintao, FENG Xilan, SHAO Mingzhe, YU Haohan, YUAN Guobao, and ZHANG Yu. Preparation of Quaternary FeCoMoCu Metal Oxides for Oxygen Evolution Reaction[J]. 高等学校化学研究, 2022, 38(3): 823-828.
[9]	LIU Shujing, GUO Jia. Two-dimensional Covalent Organic Frameworks: Intrinsic Synergy Promoting Photocatalytic Hydrogen Evolution[J]. 高等学校化学研究, 2022, 38(2): 373-381.
[10]	WANG Tianxiong, MU Zhenjie, DING Xuesong and HAN Baohang. Functionalized COFs with Quaternary Phosphonium Salt for Versatilely Catalyzing Chemical Transformations of CO₂[J]. 高等学校化学研究, 2022, 38(2): 446-455.
[11]	ZHENG Zhiqiang, HE Feng, XUE Yurui, LI Yuliang. Loading Nickel Atoms on GDY for Efficient CO₂ Fixation and Conversion[J]. 高等学校化学研究, 2022, 38(1): 92-98.
[12]	HU Guilin, HE Jingyi, LI Yongjun. Application of Graphdiyne and Its Analogues in Photocatalysis and Photoelectrochemistry[J]. 高等学校化学研究, 2021, 37(6): 1195-1212.
[13]	SONG Congying, LI Guoxing. Graphdiyne: A Versatile Material in Electrochemical Energy Conversion and Storage[J]. 高等学校化学研究, 2021, 37(6): 1224-1241.
[14]	FU Xinliang, ZHU Aonan, CHEN Xiaojie, ZHANG Shifu, WANG Mei, YUAN Mingjian. Stabilization of Cu/Ni Alloy Nanoparticles with Graphdiyne Enabling Efficient CO₂ Reduction[J]. 高等学校化学研究, 2021, 37(6): 1328-1333.
[15]	ZHANG Chao, LI Yuliang. Graphdiyne Based Atomic Catalyst: an Emerging Star for Energy Conversion[J]. 高等学校化学研究, 2021, 37(6): 1149-1157.