One-Step Synthesis of Unsymmetric 1,1'-Biaryl-2,2'-diamines by the Reaction of 2-Naphthols with Aryl Hydrazines

doi:10.6023/cjoc201707018

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (2): 443-450.DOI: 10.6023/cjoc201707018 Previous Articles Next Articles

Special Issue: 碳氢活化合辑2018-2019

Articles

通过2-萘酚与芳基肼的反应一步构筑非对称的1,1'-二芳基-2,2'-二胺化合物

贾磊, 唐强, 罗美明, 曾小明

四川大学化学学院成都 610064

收稿日期:2017-07-14 修回日期:2017-09-20 发布日期:2017-10-16
通讯作者: 罗美明, 曾小明 E-mail:luomm@scu.edu.cn;zengxiaoming@scu.edu.cn
基金资助:
国家自然科学基金（Nos.21321061，21072134，21202128，21572175，J1103315/J0104）资助项目.

One-Step Synthesis of Unsymmetric 1,1'-Biaryl-2,2'-diamines by the Reaction of 2-Naphthols with Aryl Hydrazines

Jia Lei, Tang Qiang, Luo Meiming, Zeng Xiaoming

College of Chemistry, Sichuan University, Chengdu 610064

Received:2017-07-14 Revised:2017-09-20 Published:2017-10-16
Contact: 10.6023/cjoc201707018 E-mail:luomm@scu.edu.cn;zengxiaoming@scu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21321061, 21072134, 21202128, 21572175, J1103315/J0104).

1. One-Step Synthesis of Unsymmetric 1,1'-Biaryl-2,2'-diamines by the Reaction of 2-Naphthols with Aryl Hydrazines.PDF(4481KB)

Abstract

Cite this article

Jia Lei, Tang Qiang, Luo Meiming, Zeng Xiaoming. One-Step Synthesis of Unsymmetric 1,1'-Biaryl-2,2'-diamines by the Reaction of 2-Naphthols with Aryl Hydrazines[J]. Chin. J. Org. Chem., 2018, 38(2): 443-450.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Pu, L. Chem. Rev. 1998, 98, 2405.
(b) Au-Yeung, T. T. L.; Chan, S. -S.; Chan, A. S. C. Adv. Synth. Catal. 2003, 345, 537.
(c) Che, C. -M.; Huang, J. -S. Coord. Chem. Rev. 2003, 242, 97.
(d) Kocovský, P.; Vyskocil, Š.; Smrcina, M. Chem. Rev. 2003, 103, 3213.
(e) Telfer, S. G.; Kuroda, R. Coord. Chem. Rev. 2003, 242, 33.
[2] (a) Kabuto, K.; Yoshida, T.; Yamaguchi, S.; Miyano, S.; Hashimoto, H. J. Org. Chem. 1985, 50, 3013.
(b) Sakamoto, A.; Yamamoto, Y.; Oda, J. J. Am. Chem. Soc. 1987, 109, 7188.
(c) Denmark, S. E.; Su, X.; Nishigaichi, Y.; Coe, D. M.; Wong, K. -T.; Winter, S. B. D.; Choi, J. Y. J. Org. Chem. 1999, 64, 1958.
(d) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2000, 122, 12021.
(e) Reetz, M. T.; Haderlein, G.; Angermund, K. J. Am. Chem. Soc. 2000, 122, 996.
(f) Denmark, S. E.; Beutner, G. L. J. Am. Chem. Soc. 2003, 125, 7800.
(g) Shi, M.; Wang, C. -J. Adv. Synth. Catal. 2003, 345, 971.
(h) Wang, C. -J.; Shi, M. J. Org. Chem. 2003, 68, 6229.
(i) Shi, M.; Wang, C. -J.; Zhang, W. Chem. -Eur. J. 2004, 10, 5507.
(j) Wang, J.; Li, H.; Duan, W.; Zu, L.; Wang, W. Org. Lett. 2005, 7, 4713.
(k) Colombo, F.; Benaglia, M.; Orlandi, S.; Usuelli, F.; Celentano, G. J. Org. Chem. 2006, 71, 2064.
(l) Huang, H.; Okuno, T.; Tsuda, K.; Yoshimura, M.; Kitamura, M. J. Am. Chem. Soc. 2006, 128, 8716.
(m) Yan, P.; Millard, A. C.; Wei, M.; Loew, L. M. J. Am. Chem. Soc. 2006, 128, 11030.
(n) Rampalakos, C.; Wulff, W. D. Adv. Synth. Catal. 2008, 350, 1785.
(o) Alamsetti, S. K.; Mannam, S.; Mutupandi, P.; Sekar, G. Chem. -Eur. J. 2009, 15, 1086.
(p) Galzerano, P.; Bencivenni, G.; Pesciaioli, F.; Mazzanti, A.; Giannichi, B.; Sambri, L.; Bartoli, G.; Melchiorre, P. Chem. -Eur. J. 2009, 15, 7846.
(q) Scarborough, C. C.; McDonald, R. I.; Hartmann, C.; Sazama, G. T.; Bergant, A.; Stahl, S. S. J. Org. Chem. 2009, 74, 2613.
(r) Chapurina, Y.; Hannedouche, J.; Collin, J.; Guillot, R.; Schulz, E.; Trifonov, A. Chem. Commun. 2010, 46, 6918.
(s) Chapurina, Y.; Ibrahim, H.; Guillot, R.; Kolodziej, E.; Collin, J.; Trifonov, A.; Schulz, E.; Hannedouche, J. J. Org. Chem. 2011, 76, 10163.
(t) Lovick, H. M.; An, D. K.; Livinghouse, T. S. Dalton Trans. 2011, 40, 7697.
(u) Chapurina, Y.; Guillot, R.; Lyubov, D.; Trifonov, A.; Hannedouche, J.; Schulz, E. Dalton Trans. 2013, 42, 507.
[3] Clemo, G. R.; Dawson, E. C. J. Chem. Soc. 1939, 1114.
[4] Feng, Q.; Zhang, C.; Tang, Q.; Luo, M. Chin. Chem. Lett. 2009, 20, 1150.
[5] (a) Vyskocil, Š.; Smrcina, M.; Lorenc, M.; Tišlerová, I.; Brooks, R. D.; Kulagowski, J. J.; Langer, V.; Farrugia, L. J.; Kocovský, P. J. Org. Chem. 2001, 66, 1359.
(b) Wang, K. -L.; Hu, Y.; Li, Z.; Wu, M.; Liu, Z. -H.; Su, B.; Yu, A.; Liu, Y.; Wang, Q. -M. Synthesis 2010, 1083.
(c) Li, X. -L.; Huang, J. -H.; Yang, L. -M. Org. Lett. 2011, 13, 4950.
(d) Montazeri, N.; Tavana, M.; Yousefian, S.; Firooz, F. T. Asian J. Chem. 2012, 24, 840.
[6] Lim, Y. -K.; Jung, J. -W.; Lee, H.; Cho, C. -G. J. Org. Chem. 2004, 69, 5778.
[7] Tang, Q.; Zhang, C.; Luo, M. J. Am. Chem. Soc. 2008, 130, 5840.
[8] Drake, N. L. In Organic Reactions, John Wiley & Sons, Inc., 2004.
[9] Gao, J.; Zhang, C.; Luo, M.; Kim, C.; Chu,W.; Xue, Y. J. Comput. Chem. 2012, 33, 220.
[10] (a) Bell, K. H.; McCaffery, L. F. Aust. J. Chem. 1993, 46, 731.
(b) Koelsch, F. Organic Syntheses, Coll. Vol. 3, Eds.:Bachamann, W. E.; Kush, S., Wiley, New York, 1955, pp. 132~133.
(c) Lockhart, J. C.; McDonnell, M. B.; Clegg, W.; Hill, M. N. S. J. Chem. Soc., Perkin Trans. 2 1987, 639.
(d) Kumar, R.; Ramachandran, U.; Srinivasan, K.; Ramarao, P.; Raichur, S.; Chakrabarti, R. Bioorg. Med. Chem. 2005, 13, 4279.

[1]	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.
[2]	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.
[3]	Yonghong Zhang, Chengzong Tang, Yonghong Liu, Chenjiang Liu. Research Progress of Aryltriazene as Aryl Precursor and Aryl-Azo Precursors in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2587-2600.
[4]	Hu Yongqin, Huang Danfeng, Wang Kehu, Zhao Zhuanxia, Zhao Fangxia, Xu Weigang, Hu Yulai. Study on Allylation Reactions of Trifluoromethylated Acylhydrazones with Allylsilanes or Allylboronates [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1689-1696.
[5]	Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 663-668.
[6]	Li Yi, Wan Jieping. Synthesis of 3-Alkylthiol Pyrazoles via Regioselective Annulation Reactions of Sulfonyl Hydrazines and Ketene Dithioacetals [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3889-3894.
[7]	Xu Wenzhi, Li Xue, Han Mengnan, Zhou Tingting, Yang Yutao, Li Wei. A Fluorescent Probe for Hydrazine Based on Synergistic Effect and Its Utilization in Cell Imaging [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 181-185.
[8]	Zhu Ye, Huang Jinwen, Yang Xianjin. Chlorination of Anilide by Pd(OAc)₂/N-Chloro-N-fluorobenzene- sulfonylamide [J]. Chin. J. Org. Chem., 2019, 39(6): 1665-1671.
[9]	Zhao Yu, Guan Aiying, Li Wanzhen, Wang Weiwei, Liu Xinlei, Wang Ming'an. Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives [J]. Chin. J. Org. Chem., 2019, 39(5): 1344-1353.
[10]	Yang Ziqi, Liu Xingkun, Jiang Lu'nan, Wang Mei. Design, Synthesis and Application of Fluorescence Resonance Energy Transfer-Based Ratiometric Hydrazine Fluorescent Probe [J]. Chin. J. Org. Chem., 2019, 39(5): 1483-1488.
[11]	Feng Enqi, Hou Zhongwei, Xu Haichao. Electrochemical Synthesis of Tetrasubstituted Hydrazines by Dehydrogenative N-N Bond Formation [J]. Chin. J. Org. Chem., 2019, 39(5): 1424-1428.
[12]	Cai Han, Ouyang Kunbing, Yang Nianfa. Application of Chiral 1,1'-Bi-2-naphthol Polymers in Asymmetric Epoxidation of (E)-α,β-Unsaturated Aryl Ketones [J]. Chin. J. Org. Chem., 2019, 39(5): 1456-1459.
[13]	Ju Zhiyu, Shu Penghua, Xie Zhiyu, Jiang Yuqing, Tao Weijie, Xu Zhihong. A Flavone-Based Fluorescent Probe for Hydrazine and Its Bioimaging in Live Cells [J]. Chin. J. Org. Chem., 2019, 39(3): 697-702.
[14]	Cai Tao, Yang Yu, Zhang Li, Wen Tingbin. Reactivity of Ruthenium Allenylidene Complexes with Hydrazines:Formation of Acrylonitrile Complexes [J]. Chin. J. Org. Chem., 2018, 38(8): 2017-2027.
[15]	Wu Shouqun, Li Xiaoqin, Meng Jiao, Gan Yiyuan, Tian Kun, Wang Zhenchao, Ouyang Guiping. Synthesis and Antibacterial Activity of 2-Morpholino-1-propyl-1H-indole-3-substituted Acylhydrazone Derivatives [J]. Chin. J. Org. Chem., 2018, 38(6): 1447-1453.

通过2-萘酚与芳基肼的反应一步构筑非对称的1,1'-二芳基-2,2'-二胺化合物

One-Step Synthesis of Unsymmetric 1,1'-Biaryl-2,2'-diamines by the Reaction of 2-Naphthols with Aryl Hydrazines

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments