Strong-Acid Cation Exchange Resin Catalyzed Synthesis of Bis(indolyl)methanes in Water
- Corresponding author: Xia Chengcai, xiachc@163.com
Citation:
Zhang Ruize, Wang Guodong, Li Hongshuang, Duan Guiyun, Wang Kai, Xia Chengcai. Strong-Acid Cation Exchange Resin Catalyzed Synthesis of Bis(indolyl)methanes in Water[J]. Chinese Journal of Organic Chemistry,
;2019, 39(5): 1429-1435.
doi:
10.6023/cjoc201810011
(a) Garbe, T. R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. J. Nat. Prod. 2000, 63, 596.
(b) Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. J. Nat. Prod. 1995, 58, 1254.
(a) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z. Chem Rev. 2010, 110, 2250.
(b) Bell, R.; Carmeli, S.; Sar, N. J. Nat. Prod. 1994, 57, 1587.
(c) Fahy, E.; Potts, B. C. M.; Faulkner, D. J.; Smith, K. J. Nat. Prod. 1991, 54, 564.
(d) Swetha, A.; MadhuBabu, B.; Meshram. H. M. Tetrahedron Lett. 2015, 56, 1775.
Bharate, S. B.; Bharate, J. B.; Khan, S. I.; Tekwani, B. L.; Jacob, M. R.; Mudududdla, R.; Yadav, R. R.; Singh, B.; Sharma, P. R.; Maity, S.; Singh, B.; Khan, I. A.; Vishwakarma, R. A. Eur. J. Med. Chem. 2013, 63, 435.
doi: 10.1016/j.ejmech.2013.02.024
Sarva, S.; Harinath, J. S.; Sthanikam, S. P.; Ethiraj, S.; Vaithiyalingam, M.; Cirandur, S. R. Chin. Chem. Lett. 2016, 27, 16.
doi: 10.1016/j.cclet.2015.08.012
(a) Sashidhara, K. V.; Kumar, A.; Kumar, M.; Srivastava, A.; Puri, A. Bioorg. Med. Chem. Lett. 2010, 20, 6504.
(b) Sashidhara, K. V.; Modukuri, R. K.; Sonkar, R.; Rao, K. B.; Bhatia, G. Eur. J. Med. Chem., 2013, 68, 38.
(c) Sashidhara, K. V.; Kumar, A.; Kumar, M.; Srivastava, A.; Puri, A. Bioorg. Med. Chem. Lett. 2010, 20, 6504.
Lo, K. K. W.; Tsang, K. H. K.; Hui, W. K.; Zhu, N. Chem. Commun. 2003, 2704.
(a) Mahboobi, S.; Uecker, A.; Sellmer, A.; Cénac, C.; Hö cher, H.; Pongratz, H.; Eichhorn, E.; Hufsky, H.; Trümpler, A.; Sicker, M.; Heidel, F.; Fischer, T.; Stocking, C.; Elz, S.; Bö hmer, F. D.; Dove, S. J. Med. Chem. 2006, 49, 3101.
(b) Kamal, A.; Srikanth, Y. V. V.; Ramaiah, M. J.; Khan, M. N. A.; Reddy, M. K.; Ashraf, M.; Lavanya, A.; Pushpavalli, S. N. C. V. L.; Pal-Bhadra, M. Bioorg. Med. Chem. Lett. 2012, 22, 571.
(c) Safe, S.; Papineni, S.; Chintharlapalli, S. Cancer Lett. 2008, 26, 326.
(d) Grosso, C.; Cardoso, A. L.; Lemos, A.; Varela, J.; Rodrigues, M. J.; Custodio, L. L.; Barreira, T. M. Eur. J. Med. Chem. 2015, 93, 9-15.
(e) Rahimi, M.; Huang, K.-L.; Tang, C. K. Cancer Lett. 2010, 295, 59.
(f) Li, Y. W.; VandenBoom, T. G.; Wang, Z. W.; Kong, D. J.; Ali, S.; Philip, P. A.; Sarkar, F. H. Cancer Res. 2010, 70, 1486.
(g) Dawson, M. I.; Ye, M.; Cao, X. H.; Farhana, L; Hu, Q. Y.; Zhao, Y.; Xu, L. P.; Kiselyuk, A.; Correa, R. G.; Yang, L.; Hou, T. J.; Reed, J. C.; Itkin-Ansari, P.; Levine, F., Sanner, M. F.; Fontana, J. A.; Zhang. X.-K. ChemMedChem 2009, 4, 1106.
Plimmer, J. R.; Gammon, D. W.; Ragsdale, N. N. Encyclopedia of Agrochemicals, John Wiley and Sons, New York, 2003, 3.
(a) Cherioux, F.; Guyard, L.; Audebert, P. Adv. Mater. 1998, 10, 1013.
(b) Noack, A.; Schr€oder, A.; Hartmann, H. Dyes Pigm. 2002, 57, 131.
(a) Minne, S. C.; Manalis, S. R.; Quate, C. F. Appl. Phys. Lett. 1995, 67, 3918.
(b) Seyedi, N.; Khabazzadeh, H. Res. Chem. Intermed. 2015, 41, 2603.
(c) Praveen, P. J.; Parameswaran, P. S.; Majik, M. S. Synthesis 2015, 47, 1827.
(d) Shiri, M.; Zolfigol, M. A.; Kruger, H. G.; Tanbakouchian, Z.; Chem. Rev. 2010, 110, 2250.
(a) Noland, W. E.; Kumar, H. V.; Flick, G. C.; Aspros, C. L.; Yoon, J. H.; Wilt, A. C.; Dehkordi, N.; Thao, S.; Schneerer, A. K.; Gao, S. M.; Tritch. K. J. Tetrahedron 2017, 73, 3913.
(b) Veisi, H.; Maleki, B.; Eshbala, F. H.; Veisi, H.; Masti, R.; Ashrafi, S. S.; Baghayeri, M. RSC Adv. 2014, 4, 30683.
Chhattise, P. K.; Arbuj, S. S.; Mohite, K. C.; Bhavsar, S. V.; Horne, A. S.; Handore, K. N.; Chabukswar, V. V. RSC Adv. 2014, 4, 28623.
doi: 10.1039/c4ra03419h
Ravia, K.; Krishnakumara, B.; Swaminathana, M. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 2015, 45, 1380.
doi: 10.1080/15533174.2013.862710
(a) Mendes, S. R.; Thurow, S.; Penteado, F.; Silva, M. S. D.; Gariani, R. A.; Perin, G.; Lenardã o, E. J. Green Chem. 2015, 17, 4334.
(b) Ghorbani-Vaghei, R.; Veisi, H.; Keypour, H.; Dehghani- Firouzabadi, A. A. Mol. Diversity 2010, 14, 87.
Shirini, F.; Khaligh, N. G. Chin. J. Catal. 2013. 34, 1890.
doi: 10.1016/S1872-2067(12)60669-X
Tumtin, S.; Kathing, C.; Phucho, I. T.; Nongrum, R.; Myrboh, B.; Nongkhlaw, R. J. Chin. Chem. Soc. 2015, 62, 321.
doi: 10.1002/jccs.201400221
Veisi, H.; Gholbedaghi, R.; Malakootikhah, J.; Sedrpoushan, A.; Maleki, B.; Kordestani, D. J. Heterocycl. Chem. 2010, 47, 1398.
doi: 10.1002/jhet.v47:6
Silveira, C. C.; Mendes, S. R.; Villetti, M. A.; Back, D. F.; Kaufman, T. S. Green Chem. 2012, 14, 2912.
doi: 10.1039/c2gc36131k
Liang, D. Q.; Huang, W. Z.; Yuan, L.; Ma, Y. H.; Ma, J. M.; Ning, D. M. Catal. Commun. 2014, 55, 11.
doi: 10.1016/j.catcom.2014.06.005
Jejurkar, V. P.; Khatri, C. K.; Chaturbhuj, G. U.; Saha, S. ChemistrySelect 2017, 2, 11693.
doi: 10.1002/slct.201702610
(a) Feng, X. L.; Guan, C. J.; Zhao, C. X. Synth. Commun. 2004, 34, 487.
(b) Surasania, R.; Kalitaa, D.; Chandrasekharb, K. B. Green Chem. Lett. Rev. 2013, 6, 113.
(c) Lin, Z. H.; Guan, C. J.; Feng, X. L.; Zhao, C. X. J. Mol. Catal. A: Chem. 2006, 247, 19.
Fekri, L. Z.; Nikpassand, M.; Kohansal, M. Russ. J. Gen. Chem. 2015, 85, 2861.
doi: 10.1134/S1070363215120361
Griffiths, K.; Kumar, P.; Akien, G. R.; Chilton, N. F.; Abdul-Sada, A.; Tizzard, G. J.; Coles, S. J.; Kostakis, G. E. Chem. Commun. 2016, 52, 7866.
doi: 10.1039/C6CC03608B
(a) Mobaraki, A.; Movassagh, B.; Karimi, B. Appl. Catal. A: Gen. 2014, 472, 123.
(b) Wang, A. Q.; Liu, X.; Su, Z. X.; Jing, H. W. Sci. Technol. 2014, 4, 71
(c) Rafiee, E.; Eavani, S.; Malaekeh-Nikouei, B. Chem. Lett. 2012, 41, 438.
(a) Saffar-Teluri, A. Res. Chem. Intermed. 2014, 40, 1061.
(b) Shirini, F.; Lati, M. P. J. Iran. Chem. Soc. 2017, 14, 75.
(c) Sadeghi, B.; Tavasoli, F. A.; Hassanabadi, A. Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 2015, 45, 1396.
Shi, X. L.; Lin, H. K.; Li, P. Y.; Zhang, W. Q. ChemCatChem 2014, 6, 2947.
doi: 10.1002/cctc.v6.10
Singh, N. G.; Nongrum, R.; Kathing, C.; Rani, J. W. S.; Nongkhlaw, R. Green Chem. Lett. Rev. 2014, 7, 137.
doi: 10.1080/17518253.2014.902506
Gao, G.; Han, Y.; Zhang, Z. H. ChemistrySelect 2017, 2, 11561.
doi: 10.1002/slct.201702326
Hirashita, T.; Ogawa, M.; Hattori, R.; Okochi, S.; Araki, S. Bull. Chem. Soc. Jpn. 2015, 88, 1760.
doi: 10.1246/bcsj.20150247
(a) Wu, C.; Lu, L. H.; Peng, A. Z.; Jia, G. K.; Peng, C.; Cao, Z.; Tang, Z. L.; He, W. M.; Xu, X. H. Green Chem., 2018, 20, 3683.
(b) Zou, B. Yu, B.; Hu, C. W. J. CO2 Util. 2018, 26, 314.
(c) Xie, L. Y.; Peng, S.; Lu, L. H.; Hu, J.; Bao, W. H.; Zeng, F.; Tang, Z. L.; Xu, X. H.; He, W. M. ACS Sustainable Chem. Eng. 2018, 6, 7989.
(a) Zhou, Z.; Duan, J. F.; Mu, X. J.; Xiao. S. Y. Chin. J. Org. Chem. 2018, 38, 585.
(b) Yue, H. L.; Bao, P. L.; Wang, L. L.; Lv, X. X.; Yang, D. S.; Wang, H.; Wei, W. Chin. J. Org. Chem. 2019, 39, 463.
(c) Zhao, S. Y.; Wang, Z. L. Chin. J. Org. Chem. 2016, 36, 862(in Chinese).
(赵苏艳, 王祖利, 有机化学, 2016, 36, 862.)
(d) Li, W. Y.; Yin, G. X.; Huang, L.; Xiao, Y.; Fu, Z. M.; Xin, X.; Liu, F.; Li, Z. Z.; He, W. M. Green Chem. 2016, 18, 4879.
(e) Wu, C.; Xin, X.; Fu, Z. M.; Xie, L. Y.; Liu, K. J.; Wang, Z.; Li, W. Y.; Yuan, Z. H.; He, W. M. Green Chem. 2017, 19, 1983.
Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
Wei Zhou , Xi Chen , Lin Lu , Xian-Rong Song , Mu-Jia Luo , Qiang Xiao . Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis. Chinese Chemical Letters, 2024, 35(4): 108902-. doi: 10.1016/j.cclet.2023.108902
Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862
Rui Wang , Yuan Tian , Xuefeng Gao , Lei Jiang . Design and fabrication of triangle-pattern superwettability hybrid surface with high-efficiency condensation heat transfer performance. Chinese Chemical Letters, 2025, 36(3): 110395-. doi: 10.1016/j.cclet.2024.110395
Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
Yunxia Liu , Guandong Wu , Lin Li , Yiming Niu , Bingsen Zhang , Botao Qiao , Junhu Wang . Construction of sintering-resistant gold catalysts via ascorbic-acid inducing strong metal-support interactions. Chinese Chemical Letters, 2025, 36(4): 110608-. doi: 10.1016/j.cclet.2024.110608
Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
Zhaoru Chen , Xiaoxu Liu , Haonan Chen , Jialong Li , Xiaofeng Wang , Jianfeng Zhu . Application of epoxy resin in cultural relics protection. Chinese Chemical Letters, 2024, 35(4): 109194-. doi: 10.1016/j.cclet.2023.109194
Yanbing Shen , Yuan Yuan , Yaxin Wang , Xiaonan Ma , Wensheng Yang , Yulan Chen . Dihydroanthracene bridged bis-naphthopyrans: A multimodal chromophore with mechano- and photo-chromic properties. Chinese Chemical Letters, 2024, 35(5): 108949-. doi: 10.1016/j.cclet.2023.108949
Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
Jing Wang , Zenghui Li , Xiaoyang Liu , Bochao Su , Honghong Gong , Chao Feng , Guoping Li , Gang He , Bin Rao . Fine-tuning redox ability of arylene-bridged bis(benzimidazolium) for electrochromism and visible-light photocatalysis. Chinese Chemical Letters, 2024, 35(9): 109473-. doi: 10.1016/j.cclet.2023.109473
Hao Jiang , Yuan-Yuan He , Hai-Chao Liang , Meng-Jia Shang , Han-Han Lu , Chun-Hua Liu , Yin-Shan Meng , Tao Liu , Yuan-Yuan Zhu . Tuning lanthanide luminescence from bipyridine-bis(oxazoline/thiazoline) tetradentate ligands. Chinese Journal of Structural Chemistry, 2024, 43(9): 100354-100354. doi: 10.1016/j.cjsc.2024.100354
Gaofeng WANG , Shuwen SUN , Yanfei ZHAO , Lixin MENG , Bohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479
Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO2 cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
Heng Gao , Zhaocong Cheng , Guangshui Tu , Zonglin Qiu , Xieyi Xiao , Haotian Zhou , Handou Zheng , Haiyang Gao . Thermally robust bis(imino)pyridyl iron catalysts for ethylene polymerization: Synergy effects of weak π-π interaction, steric bulk, and electronic tuning. Chinese Chemical Letters, 2025, 36(5): 110762-. doi: 10.1016/j.cclet.2024.110762
Yuan Dong , Mutian Ma , Zhenyang Jiao , Sheng Han , Likun Xiong , Zhao Deng , Yang Peng . Effect of electrolyte cation-mediated mechanism on electrocatalytic carbon dioxide reduction. Chinese Chemical Letters, 2024, 35(7): 109049-. doi: 10.1016/j.cclet.2023.109049
Yinghui Xia , Yixi Lin , Zhenming Xu . Cation potential guiding structural regulation of lithium halide superionic conductors. Chinese Journal of Structural Chemistry, 2025, 44(3): 100448-100448. doi: 10.1016/j.cjsc.2024.100448
Junchuan Sun , Lu Wang . Carbon exchange enabled supra-photothermal methane dry reforming. Chinese Journal of Structural Chemistry, 2024, 43(10): 100330-100330. doi: 10.1016/j.cjsc.2024.100330