Research Progress in the Cycloaddition Reactions of Aziridines

doi:10.6023/cjoc201511039

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 939-953.DOI: 10.6023/cjoc201511039 Previous Articles Next Articles

REVIEW

氮杂环丙烷环加成反应的研究进展

王清宇, 常宏宏, 魏文珑, 刘强, 高文超, 李彦威, 李兴

太原理工大学化学化工学院生物与制药工程系太原 030024

收稿日期:2015-11-19 修回日期:2015-12-25 发布日期:2016-01-15
通讯作者: 李彦威, 李兴 E-mail:yanweili59@126.com;lixing@tyut.edu.cn
基金资助:
山西省自然科学基金(No.2012021007-2)资助项目.

Research Progress in the Cycloaddition Reactions of Aziridines

Wang Qingyu, Chang Honghong, Wei Wenlong, Liu Qiang, Gao Wenchao, Li Yanwei, Li Xing

College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Received:2015-11-19 Revised:2015-12-25 Published:2016-01-15
Supported by:
Project supported by the Natural Science Foundation of Shanxi Province (No. 2012021007-2).

Cite this article

Wang Qingyu, Chang Honghong, Wei Wenlong, Liu Qiang, Gao Wenchao, Li Yanwei, Li Xing. Research Progress in the Cycloaddition Reactions of Aziridines[J]. Chin. J. Org. Chem., 2016, 36(5): 939-953.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Brichacek, M.; Lee, D. E.; Njardarson, J. T. Org. Lett. 2008, 10, 5023.
[2] Li, L.; Wu, X.; Zhang, J. Chem. Commun. 2011, 47, 5049.
[3] Lowe, M. A.; Ostovar, M.; Ferrini, S.; Chen, C. C.; Lawrence, P. G.; Fontana, F.; Calabrese, A. A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2011, 50, 6370.
[4] Griffin, K.; Montagne, C.; Hoang, C. T.; Clarkson, G. J.; Shipman, M. Org. Biomol. Chem. 2012, 10, 1032.
[5] Arena, G.; Chen, C. C.; Leonori, D.; Aggarwal, V. K. Org. Lett.2013, 15, 4250.
[6] Takahashi, H.; Yasui, S.; Tsunoi, S.; Shibata, I. Org. Lett. 2014, 16, 1192.
[7] Martinand-Lurin, E.; Gruber, R.; Retailleau, P.; Fleurat-Lessard, P.; Dauban, P. J. Org. Chem.2015, 80, 1414.
[8] Xu, C. F.; Zheng, B. H.; Suo, J. J.; Ding, C. H.; Hou, X. L. Angew. Chem., Int. Ed. 2015, 54, 1604.
[9] Wang, L.; Yang, D.; Han, F.; Li, D.; Zhao, D.; Wang, R. Org. Lett. 2015, 17, 176.
[10] Huang, Y.; Zheng, C.; Pan, L.; Jin, Q.; Zhao, G. J. Org. Chem. 2015, 80, 10710.
[11] Zhu, W.; Cai, G.; Ma, D. Org. Lett.2005, 7, 5545.
[12] Wender, P. A.; Strand, D. J. Am. Chem. Soc. 2009, 131, 7528.
[13] Fan, J.; Gao, L.; Wang, Z. Chem. Commun. 2009, 5021.
[14] Zhao, X.; Zhang, E.; Tu, Y. Q.; Zhang, Y. Q.; Yuan, D. Y.; Cao, K.; Fan, C. A.; Zhang, F. M. Org. Lett. 2009,11, 4002.
[15] Khlebnikov, A. F.; Novikov, M. S.; Petrovskii, P. P.; Konev, A. S.; Yufit, D. S.; Selivanov, S. I.; Frauendorf, H. J. Org. Chem. 2010, 75, 5211.
[16] Li, L.; Zhang, J. Org. Lett. 2011, 13, 5840.
[17] Kim, M. S.; Kim, Y. W.; Hahm, H. S.; Jang, J. W.; Lee, W. K.; Ha, H. J. Chem. Commun. 2005, 3062.
[18] Jiang, Z.; Wang, J.; Lu, P.; Wang, Y. Tetrahedron2011, 67, 9609.
[19] Wu, X.; Zhang, J. Synthesis 2012, 44, 2147.
[20] Yadav, V. K.; Sriramurthy, V. J. Am. Chem. Soc. 2005, 127, 16366.
[21] Ghorai, M. K.; Ghosh, K.; Das, K. Tetrahedron Lett. 2006, 47, 5399.
[22] Wu, J.; Sun, X.; Xia, H. G. Tetrahedron Lett. 2006, 47, 1509.
[23] Yadav, J. S.; Subba Reddy, B. V.; Pandurangam, T.; Subba Reddy, U. V. Chem. Lett. 2008, 37, 824.
[24] Li, X.; Yang, X.; Chang, H.; Li, Y.; Ni, B.; Wei, W. Eur. J. Org. Chem.2011, 3122.
[25] Yoshiki, M.; Ishibashi, R.; Yamada, Y.; Hanamoto, T. Org. Lett. 2014, 16, 5509.
[26] Ghorai, M. K.; Ghosh, K. Tetrahedron Lett. 2007, 48, 3191.
[27] Kang, B.; Miller, A. W.; Goyal, S.; Nguyen, S. T. Chem. Commun. 2009, 3928.
[28] Maeda, R.; Ishibashi, R.; Kamaishi, R.; Hirotaki, K.; Furuno, H.; Hanamoto, T. Org. Lett. 2011, 13, 6240.
[29] Wu, X.; Li, L.; Zhang, J. Chem. Commun. 2011, 47, 7824.
[30] Yang, H. T.; Xing, M. L.; Zhu, Y. F.; Sun, X. Q.; Cheng, J.; Miao, C. B.; Li, F. B. J. Org. Chem. 2014, 79, 1487.
[31] Du, Y.; Wu, Y.; Liu, A. H.; He, L. N. J. Org. Chem. 2008, 73, 4709.
[32] Wu, Y.; He, L. N.; Du, Y.; Wang, J. Q.; Miao, C. X.; Li, W. Tetrahedron 2009, 65, 6204.
[33] Zhao, Y. N.; Yang, Z. Z.; Luo, S. H.; He, L. N. Catal. Today 2013, 200, 2.
[34] Dou, X. Y.; He, L. N.; Yang, Z. Z.; Wang, J. L. Synlett 2010, 2159.
[35] Phung, C.; Ulrich, R. M.; Ibrahim, M.; Tighe, N. T. G.; Lieberman, D. L.; Pinhas, A. R. Green Chem. 2011, 13, 3224.
[36] Wu, Y.; Liu, G. Tetrahedron Lett. 2011, 52, 6450.
[37] Fontana, F.; Chen, C. C.; Aggarwal, V. K. Org. Lett. 2011, 13, 3454.
[38] Seayad, J.; Seayad, A. M.; Ng, J. K. P.; Chai, C. L. L. ChemCatChem 2012, 4, 774.
[39] Ueno, A.; Kayaki, Y.; Ikariya, T. Green Chem. 2013, 15, 425.
[40] Nale, D. B.; Rana, S.; Parida, K.; Bhanage, B. M. Appl. Catal. A: Gen.2014, 469, 340.
[41] Chen, W.; Zhong, L.; Peng, X.; Sun, R.; Lu, F. ACS Sustainable Chem. Eng. 2015, 3, 147.
[42] Wu, J. Y.; Luo, Z. B; Dai, L. X.; Hou, X. L. J. Org. Chem. 2008, 73, 9137.
[43] Chen, N.; Jia, W.; Xu, J. Eur. J. Org. Chem. 2009, 5841.
[44] Sengoden, M.; Punniyamurthy, T. Angew. Chem., Int. Ed.2013, 52, 572.
[45] Cui, S. L.; Wang, J.; Wang, Y. G. Org. Lett. 2008, 10, 13.
[46] Ghorai, M. K.; Tiwari, D. P. J. Org. Chem. 2010, 75, 6173.
[47] Ghorai, M. K.; Tiwari, D. P. J. Org. Chem. 2013, 78, 2617.
[48] Munegumi, T.; Azumaya, I.; Kato, T.; Masu, H.; Saito, S. Org. Lett. 2006, 8, 379.
[49] Sengoden, M.; Vijay, M.; Balakumar, E.; Punniyamurthy, T. RSC Adv. 2014, 4, 54149.
[50] Craig, R. A.; O'Connor, N. R.; Goldberg, A. F. G.; Stoltz, B. M. Chem. Eur. J.2014, 20, 4806.
[51] Goodenough, K. M.; Raubo, P.; Harrity, J. P. A. Org. Lett. 2005, 7, 2993.
[52] Wang, L.; Liu, Q. B.; Wang, D. S.; Li, X.; Han, X. W.; Xiao, W. J.; Zhou, Y. G. Org. Lett. 2009, 11, 1119.
[53] Bera, M.; Roy, S. J. Org. Chem. 2009, 74, 8814.
[54] Ghorai, M. K.; Shukla, D.; Das, K. J. Org. Chem. 2009, 74, 7013.
[55] Guo, H.; Xu, Q.; Kwon, O. J. Am. Chem. Soc. 2009, 131, 6318.
[56] Ghorai, M. K.; Nanaji, Y.; Yadav, A. K. Org. Lett. 2011, 13, 4256.
[57] Wang, S.; Chai, Z.; Zhou, S.; Wang, S.; Zhu, X.; We, Y. Org. Lett. 2013, 15, 2628.
[58] Wang, L.; Yang, D.; Li, D.; Wang, R. Org. Lett.2015, 17, 3004.
[59] Chouhan, G.; Alper, H. Org. Lett.2010, 12, 192.
[60] Ghorai, M. K.; Sahoo, A. K.; Bhattacharyya, A. J. Org. Chem. 2014, 79, 6468.
[61] Zhou, M. B.; Song, R. J.; Li, J. H. Angew. Chem., Int. Ed.2014, 53, 4196.
[62] Kanno, E.; Yamanoi, K.; Koya, S.; Azumaya, I.; Masu, H.; Yamasaki, R.; Saito, S. J. Org. Chem.2012, 77, 2142.
[63] Feng, J. J.; Lin, T. Y.; Wu, H. H.; Zhang, J. J. Am. Chem. Soc. 2015, 137, 3787.
[64] Shintani, R.; Ikehata, K.; Hayashi, T. J. Org. Chem. 2011, 76, 4776.

氮杂环丙烷环加成反应的研究进展

Research Progress in the Cycloaddition Reactions of Aziridines

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[2]	Mengzhu Li, Boying Meng, Wenjie Lan, Bin Fu. Synthesis of 2,3-Disubstituted Dihydrobenzofurans from o-Quinone Methides and Sulfur Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 195-203.
[3]	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.
[4]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[5]	Jun Ding, Xiaokun Shi, Yu Hao, Heyuan Bai, Shuyu Zhang. Silver-Catalyzed Enantioselective Intermolecular γ-Amination of β,γ-Unsaturated Amide [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2946-2952.
[6]	Xinqiang Chen, Jing Zhang. Progress in the Study of Dehydroxymethylation of Primary Alcohol [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2711-2719.
[7]	Yi Wang, Jian Zhang, Yangzi Liu, Xiaoyan Luo, Weiping Deng. Palladium-Catalyzed Asymmetric [3＋4] Cycloadditions for the Construction of Cyclohepta[b]indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2864-2877.
[8]	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.
[9]	Deliang Kong, Wen Dai, Yiling Zhao, Yilin Chen, Hongping Zhu. Study on Oxidative Cycloaddition Reactions of Amidinatoboryl-aminosilylenes toward Ketone and Diketone Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1843-1851.
[10]	Fang Wei, Xin Yu, Qiang Xiao. Advances in C—N₃ Retention Reactions Involving Organic Azides [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1365-1385.
[11]	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.
[12]	Chunbo Dai, Siqi Xia, Xiaoyu Chen, Limin Yang. N-Heterocyclic Carbene (NHC)-Catalyzed [4+3] Cycloaddition to Synthesize 4-Aminobenzoheptenolactons [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1084-1090.
[13]	Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.
[14]	Haiqing Wang, Shuang Yang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxybenzyl Alcohols [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 974-999.
[15]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.