Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 443-450. doi: 10.6023/cjoc201707018 shu

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

College of Chemistry, Sichuan University, Chengdu 610064

Corresponding author: Luo Meiming, luomm@scu.edu.cn Zeng Xiaoming, zengxiaoming@scu.edu.cn
Received Date: 14 July 2017
Revised Date: 20 September 2017
Available Online: 16 February 2017
Fund Project: the National Natural Science Foundation of China 21572175the National Natural Science Foundation of China 21321061Project supported by the National Natural Science Foundation of China (Nos. 21321061, 21072134, 21202128, 21572175, J1103315/J0104)the National Natural Science Foundation of China 21072134the National Natural Science Foundation of China 21202128the National Natural Science Foundation of China J1103315/J0104

Figures(2)

A metal-free, operationally simple synthetic protocol for the buildup of unsymmetric 1, 1'-biaryl-2, 2'-diamine compounds was reported. This reaction was performed by the treatment of 2-naphthols with aryl hydrazines under no transition metal catalyst and no ligand conditions, which has the advantages of simple operation and one-step synthesis.
- 1, 1'-biaryl-2, 2'-diamine,
- 2-naphthol,
- hydrazine,
- synthetic methodology
1. [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) Kočovský, P. ; Vyskočil, Š. ; Smrčina, M. Chem. Rev. 2003, 103, 3213.
  (e) Telfer, S. G. ; Kuroda, R. Coord. Chem. Rev. 2003, 242, 33.
2. [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. [3]
  Clemo, G. R.; Dawson, E. C. J. Chem. Soc. 1939, 1114. doi: 10.1039/jr9390001114
4. [4]
  Feng, Q.; Zhang, C.; Tang, Q.; Luo, M. Chin. Chem. Lett. 2009, 20, 1150. doi: 10.1016/j.cclet.2009.05.033
5. [5]
  (a) Vyskočil, Š. ; Smrčina, M. ; Lorenc, M. ; Tišlerová, I. ; Brooks, R. D. ; Kulagowski, J. J. ; Langer, V. ; Farrugia, L. J. ; Kočovský, 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. [6]
  Lim, Y. -K.; Jung, J. -W.; Lee, H.; Cho, C. -G. J. Org. Chem. 2004, 69, 5778. doi: 10.1021/jo049270g
7. [7]
  Tang, Q.; Zhang, C.; Luo, M. J. Am. Chem. Soc. 2008, 130, 5840. doi: 10.1021/ja711153b
8. [8]
  Drake, N. L. In Organic Reactions, John Wiley & Sons, Inc., 2004.
9. [9]
  Gao, J.; Zhang, C.; Luo, M.; Kim, C.; Chu, W.; Xue, Y. J. Comput. Chem. 2012, 33, 220. doi: 10.1002/jcc.v33.2
10. [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. [1]
  Gang Lang , Jing Feng , Bo Feng , Junlan Hu , Zhiling Ran , Zhiting Zhou , Zhenju Jiang , Yunxiang He , Junling Guo . Supramolecular phenolic network-engineered C–CeO₂ nanofibers for simultaneous determination of isoniazid and hydrazine in biological fluids. Chinese Chemical Letters, 2024, 35(6): 109113-. doi: 10.1016/j.cclet.2023.109113
2. [2]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
3. [3]
  Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
4. [4]
  Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A₂-A₁-D-A₁-A₂ type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
5. [5]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
6. [6]
  Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO₂ reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112
7. [7]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
8. [8]
  Wen-Tao Ouyang , Jun Jiang , Yan-Fang Jiang , Ting Li , Yuan-Yuan Liu , Hong-Tao Ji , Li-Juan Ou , Wei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038
9. [9]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
10. [10]
  Yu Xiong , Li-Jun Hu , Jian-Guo Song , Di Zhang , Yi-Shuang Peng , Xiao-Jun Huang , Jian Hong , Bin Zhu , Wen-Cai Ye , Ying Wang . Structure elucidation of plumerubradins A–C: Correlations between ¹H NMR signal patterns and structural information of [2+2]-type cyclobutane derivatives. Chinese Chemical Letters, 2025, 36(5): 110149-. doi: 10.1016/j.cclet.2024.110149
11. [11]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
12. [12]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
13. [13]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
14. [14]
  Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
15. [15]
  Fuyun Chi , Man Zhang , Yiman Han , Fukui Shen , Shijie Peng , Bo Su , Yuanyuan Hou , Gang Bai . Covalent modulation of mPGES1 activity via α,β-unsaturated aldehyde group: Implications for downregulating PGE2 expression and antipyretic response. Chinese Chemical Letters, 2025, 36(4): 109913-. doi: 10.1016/j.cclet.2024.109913
16. [16]
  Liang Lou , Xuncheng Liu , Yuanyu Wang , Tao Hu , Zhongjie Wang , Houqiang Shi , Junkai Xiong , Siqi Jing , Liankang Ye , Qihui Guo , Xiang Ge . Achieving reusability of leachate for multi-element recovery of the discarded LiNi_xCo_yMn_1-x-yO₂ cathode by regulating the co-precipitation coefficient. Chinese Chemical Letters, 2025, 36(5): 109726-. doi: 10.1016/j.cclet.2024.109726
17. [17]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
18. [18]
  Ze-Yuan Ma , Mei Xiao , Cheng-Kun Li , Adedamola Shoberu , Jian-Ping Zou . S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076
19. [19]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
20. [20]
  Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr_1-xZrSi₂O₇∶xDy³⁺ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096

Get Citation

PDF

XML

Metrics

PDF Downloads(15)
Abstract views(2586)
HTML views(522)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142