Convenient Synthesis of Imidazo-Fused Heterocycles via CeCl3·7H2O Catalyzed Groebke-Blackburn-Bienayme Reaction
- Corresponding author: Guo Changbin, guocb@cnu.edu.cn
Citation:
Zhang Zhaorui, Xu Liang, Tang Hanqin, Wu Boxin, Feng Di, Guo Changbin. Convenient Synthesis of Imidazo-Fused Heterocycles via CeCl3·7H2O Catalyzed Groebke-Blackburn-Bienayme Reaction[J]. Chinese Journal of Organic Chemistry,
;2017, 37(5): 1252-1257.
doi:
10.6023/cjoc201701024
(a) Ma, Z. ; Xiang, Z. ; Luo, T. ; Lu, K. ; Xu, Z. ; Chen, J. ; Yang, Z. J. Comb. Chem. 2006, 8, 696. (b) Riva, R. ; Banfi, L. ; Basso, A. ; Cerulli, V. ; Guanti, G. ; Pani, M. J. Org. Chem. 2010, 15, 5134. (c) Erb, W. ; Neuville, L. ; Zhu, J. J. Org. Chem. 2009, 74, 3109. (d) Zhang, Z. R. ; Zheng, X. L. ; Guo, C. B. Chin. J. Org. Chem. 2016, 36, 1241 (in Chinese). (张钊瑞, 郑晓霖, 郭长彬, 有机化学, 2016, 36, 1241. )(e) Singh, S. ; Samanta, S. Chin. J. Chem. 2015, 33, 1244. (f) Wang, H. ; Xu, B. Chin. J. Org. Chem. 2015, 35, 588 (in Chinese). (王浩, 许斌, 有机化学, 2015, 35, 588. )(g) Sun, X. Y. ; Wang, W. M. ; Ma, J. ; Yu, S. Y. Acta Chim. Sinica 2017, 75, 115 (in Chinese). (孙晓阳, 王文敏, 马晶, 俞寿云, 化学学报, 2017, 75, 115. )(h) Ren, S. B. ; Zhang, H. F. ; Zhang, J. ; Zhang, W. ; Liu, Y. K. Chin. J. Org. Chem. 2016, 36, 1954 (in Chinese). (任少波, 张海峰, 张剑, 张巍, 刘运奎, 有机化学, 2016, 36, 1954. )(i) Xu, W. S. ; Zhao, S. J. ; Luo, X. P. ; Song, J. N. ; Liu, J. Q. ; Bi, X. H. ; Liao, P. Q. Chin. J. Org. Chem. 2015, 35, 2095 (in Chinese). (徐文帅, 赵寿经, 骆晓沛, 宋金娜, 刘建全, 毕锡和, 廖沛球, 有机化学, 2015, 35, 2095. )(j) Li, Z. H. ; Yan, N. N. ; Xie, J. W. ; Liu, P. ; Zhang, J. ; Dai, B. Chin. J. Chem. 2015, 33, 589.
Devi, N.; Rawal, R. K.; Singh, V. Tetrahedron 2015, 71, 183.
doi: 10.1016/j.tet.2014.10.032
Berson, A.; Descatoire, V.; Sutton, A.; Fau, D.; Maulny, B.; Vadrot, N.; Feldmann, G.; Berthon, B.; Tordjmann, T.; Pessayre, D. J. Pharmacol. Exp. Ther. 2001, 299, 793.
Harrison, T. S.; Keating, G. M. CNS Drugs 2005, 19, 65.
doi: 10.2165/00023210-200519010-00008
Kaminski, J. J.; Wallmark, B.; Briving, C.; Andersson, B. M. J. Med. Chem. 1991, 34, 533.
doi: 10.1021/jm00106a008
Mizushige, K.; Ueda, T.; Yukiiri, K.; Suzuki, H. Cardiovasc. Drug Rev. 2002, 20, 163.
(a) Palmer, A. M.; Chrismann, S.; Munch, G.; Brehm, C.; Zimmermann, P. J.; Buhr, W.; Senn-Bilfinger, J.; Feth, M. P.; Simon, W. A. Bioorg. Med. Chem. 2009, 17, 368.(b) Mori, H.; Tanaka, M.; Kayasuga, R.; Masuda, T.; Ochi, Y.; Yamada, H.; Kishikawa, K.; Ito, M.; Nakamura, T. Bone 2008, 43, 840.
Sharma, A.; Li, H. Y. Synlett 2011, 1407.
Huang, Y.; Hu, X. Q.; Shen, D. P.; Chen, Y. F.; Xu, P. F. Mol. Diversity 2007, 11, 73.
doi: 10.1007/s11030-007-9059-3
Groebke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
Che, C.; Xiang, J.; Wang, G. X.; Fathi, R.; Quan, J. M.; Yang, Z. J. Comb. Chem. 2007, 9, 982.
Mert-Balci, F.; Conrad, J.; Meindl, K.; Schulz, T.; Stalke, D.; Beifuss, U. Synthesis 2008, 3649.
McKeown, M. R.; Shaw, D. L.; Fu, H.; Liu, S.; Xu, X.; Marineau, J. J.; Huang, Y.; Zhang, X.; Buckley, D. L.; Kadam, A.; Zhang, Z.; Blacklow, S. C.; Qi, J.; Zhang, W.; Bradner, J. E. J. Med. Chem. 2014, 57, 9019.
doi: 10.1021/jm501120z
Shaabani, A.; Soleimani, E.; Sarvary, A.; Rezayan, H.; Maleki, A. Chin. J. Chem. 2009, 27, 369.
doi: 10.1002/cjoc.v27:2
Xi, G. L.; Liu, Z. Q. Tetrahedron 2015, 71, 9602.
doi: 10.1016/j.tet.2015.10.080
Shinde, A. H.; Srilaxmi, M.; Satpathi, B.; Sharada, D. S. Tetrahedron Lett. 2014, 55, 5915.
doi: 10.1016/j.tetlet.2014.08.126
Odell, L. R.; Nilsson, M.; Gising, J.; Lagerlund, O.; Muthas, D.; Nordqvist, A.; Karlen, A.; Larhed, M. Bioorg. Med. Chem. Lett. 2009, 19, 4790.
doi: 10.1016/j.bmcl.2009.06.045
Guchhait, S. K.; Madaan, C. Tetrahedron Lett. 2011, 52, 56.
doi: 10.1016/j.tetlet.2010.10.143
Guchhait, S. K.; Maadan, C. Synlett 2009, 628.
Rousseau, A. L.; Matlaba, P.; Parkinson, C. J. Tetrahedron Lett. 2007, 48, 4079.
doi: 10.1016/j.tetlet.2007.04.008
Rostamnia, S.; Hassankhanib, A. RSC Adv. 2013, 3, 18626.
doi: 10.1039/C2RA22527A
Akbarzadeh, R.; Shakibaei, G. I.; Bazgir, A. Monatsh. Chem. 2010, 141, 1077.
doi: 10.1007/s00706-010-0372-7
Sanaeishoara, T.; Tavakkolia, H.; Mohave, F. Appl. Catal., A 2014, 470, 56.
doi: 10.1016/j.apcata.2013.10.026
Shaabani, A.; Soleimani, E.; Maleki, A. Tetrahedron Lett. 2006, 47, 3031.
Lee, C. H.; Hsu, W. S.; Chen, C. H.; Sun, C. M. Eur. J. Org. Chem. 2013, 11, 2201.
Neochoritis, C. G.; Stotani, S.; Mishra, B.; Domling, A. Org. Lett. 2015, 17, 2002.
doi: 10.1021/acs.orglett.5b00759
Kolo, K.; Sajadi, S. M. Lett. Org. Chem. 2013, 10, 688.
doi: 10.2174/15701786113109990021
Bartoli, G.; Marcantoni, E.; Marcolini, M.; Sambri, L. Chem. Rev. 2010, 110, 6104.
doi: 10.1021/cr100084g
Hongzhi Zhang , Hong Li , Asif Ali Haider , Junpeng Li , Zhi Xie , Hongming Jiang , Conglin Liu , Rui Wang , Jing Zhu . An unexpected role of lanthanide substitution in thermally responsive phosphors NaLnTe2O7: Eu3+ (Ln = Y and Gd). Chinese Journal of Structural Chemistry, 2025, 44(2): 100509-100509. doi: 10.1016/j.cjsc.2024.100509
Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H3PW12O40高效催化MgH2储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
Xuewei BA , Cheng CHENG , Huaikang ZHANG , Deqing ZHANG , Shuhua LI . Preparation and luminescent performance of Sr1-xZrSi2O7∶xDy3+ phosphor with high thermal stability. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 357-364. doi: 10.11862/CJIC.20240096
Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe2O3/TiO2 heterojunction for enhanced photo-Fenton activity with low H2O2 consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe2O3 and NO2 with 2D-COS: The role of SDS, UV and SO2. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H2O and Its Intermediates on Electron-Deficient Mn(3+δ)+ for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
Yubang Li , Xixi Hu , Daiqian Xie . The microscopic formation mechanism of O + H2 products from photodissociation of H2O. Chinese Journal of Structural Chemistry, 2024, 43(5): 100274-100274. doi: 10.1016/j.cjsc.2024.100274
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
Yang Xia , Kangyan Zhang , Heng Yang , Lijuan Shi , Qun Yi . 构建双通道路径增强iCOF/Bi2O3 S型异质结在纯水体系中光催化合成H2O2性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407012-. doi: 10.3866/PKU.WHXB202407012
Chen-Chang Cui , Shao-Qing Shi , Lu-Yao Wang , Feng Lin , Man-Su Tu , Wen-Juan Hao , Bo Jiang . Accessing polyarene-fused ten-membered lactams via oxidative N-heterocyclic carbene (NHC)-catalyzed high-order [7 + 3] annulation. Chinese Chemical Letters, 2025, 36(6): 110541-. doi: 10.1016/j.cclet.2024.110541
Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C3N4纳米片及其高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H2O2 system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H2O2 for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
Huizhong Wu , Ruiheng Liang , Ge Song , Zhongzheng Hu , Xuyang Zhang , Minghua Zhou . Enhanced interfacial charge transfer on Bi metal@defective Bi2Sn2O7 quantum dots towards improved full-spectrum photocatalysis: A combined experimental and theoretical investigation. Chinese Chemical Letters, 2024, 35(6): 109131-. doi: 10.1016/j.cclet.2023.109131
Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr2O72− based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281