Enantioselective Synthesis of Triarylmethanes Bearing Pyrazole Moiety through Squaramide-Catalyzed Addition of Azadienes with Pyrazolin-5-ones
- Corresponding author: Zhou Yonggui, ygzhou@dicp.ac.cn
Citation:
Xie Huanping, Wu Bo, Chen Muwang, Yu Changbin, Li Hongwang, Li Xiang, Zhou Yonggui. Enantioselective Synthesis of Triarylmethanes Bearing Pyrazole Moiety through Squaramide-Catalyzed Addition of Azadienes with Pyrazolin-5-ones[J]. Chinese Journal of Organic Chemistry,
;2020, 40(10): 3452-3462.
doi:
10.6023/cjoc202003005
(a) Finocchiaro, P.; Gust, D.; Mislow, K. J. Am. Chem. Soc. 1974, 96, 3198.
(b) Dothager, R. S.; Putt, K. S.; Allen, B. J.; Leslie, B. J.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2005, 127, 8686.
(c) Palchaudhuri, R.; Nesterenko, V.; Hergenrother, P. J. J. Am. Chem. Soc. 2008, 130, 10274.
(d) Gemma, S.; Campiani, G.; Butini, S.; Kukreja, G.; Joshi, B. P.; Persico, M.; Catalanotti, B.; Novellino, E.; Fattorusso, E.; Nacci, V.; Savini, L.; Taramelli, D.; Basilico, N.; Morace, G.; Yardley, V.; Fattorusso, C. J. Med. Chem. 2007, 50, 595.
(e) Snyder, S. A.; Breazzano, S. P.; Ross, A. G.; Lin, Y.; Zografos, A. L. J. Am. Chem. Soc. 2009, 131, 1753.
(f) Mibu, N.; Yokomizo, K.; Uyeda, M.; Sumoto, K. Chem. Pharm. Bull. 2005, 53, 1171.
(g) Mibu, N.; Yokomizo, K.; Miyata, T.; Sumoto, K. J. Heterocycl. Chem. 2010, 47, 1434.
(h) Panda, G.; Shagufta; Mishra, J. K.; Chaturvedi, V.; Srivastava, A. K.; Srivastava, R.; Srivastava, B. S. Bioorg. Med. Chem. 2004, 12, 5269.
(i) Panda, G.; Shagufta; Srivastava, A. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2005, 15, 5222.
(j) Kashyap, V. K.; Gupta, R. K.; Shrivastava, R.; Srivastava, B. S.; Srivastava, R.; Parai, M. K.; Singh, P.; Bera, S.; Panda, G. J. Antimicrob. Chemother. 2012, 67, 1188.
For reviews of triarylmethanes and hetero-triarylmethanes, see: (a) Duxbury, D. F. Chem. Rev. 1993, 93, 381.
(b) Mondal, S.; Panda, G. RSC Adv. 2014, 4, 28317.
(c) Mondal, S.; Roy, D.; Panda, G. ChemCatChem 2018, 10, 1941.
For selected examples of bioactive hetero-triarylmethanes: (a) Whitesitt, C. A.; Whitehead, C. W. J. Med. Chem. 1974, 17, 1298.
(b) Parai, M. K.; Panda, G.; Chaturvedi, V.; Manju, Y. K.; Sinha, S. Bioorg. Med. Chem. Lett. 2008, 18, 289.
(c) Yin, L.; Hu, Q.; Hartmann, R. W. J. Med. Chem. 2013, 56, 460.
Selected examples of bioactive pyrazoles: (a) Fujimori, Y.; Katsuno, K.; Nakashima, I.; Ishikawa-Takemura, Y.; Fujikura, H.; Isaji, M. J. Pharmacol. Exp. Ther. 2008, 327, 268.
(b) Enders, D.; Grossmann, A.; Gieraths, B.; Düzdemir, M.; Merkens, C. Org. Lett. 2012, 14, 4254.
(c) Hack, D.; Chauhan, P.; Deckers, K.; Mizutani, Y.; Raabea, G.; Enders, D. Chem. Commun. 2015, 51, 2266.
(d) Prasanna, S.; Manivannan, E.; Chaturvedi, S. C. Bioorg. Med. Chem. Lett. 2005, 15, 2097.
Yetra, S. R.; Mondal, S.; Suresh, E.; Biju, A. T. Org. Lett. 2015, 17, 1417.
doi: 10.1021/acs.orglett.5b00293
(a) Vetica, F.; Bailey, S.; Chauhan, P.; Turberg, M.; Ghaur, A.; Raabe, G.; Enders, D. Adv. Synth. Catal. 2017, 359, 3729.
(b) Bao, X.; Wei, S.; Qu, J.; Wang, B. Chem. Commun. 2018, 54, 2028.
(c) Sharma, V.; Kaur, A.; Sahoo, S. C.; Chimni, S. S. Org. Biomol. Chem. 2018, 16, 6470.
(a) Kumarswamyreddy, N.; Kesavan, V. Org. Lett. 2016, 18, 1354.
(b) Luo, W.; Song, D.; Fang, L.; Nian, S.; Hou, H.; Ling, F.; Zhong, W. Asian J. Org. Chem. 2018, 7, 2417.
(c) Sharma, A.; Sharma, V.; Chimni, S. S. Org. Biomol. Chem. 2019, 17, 9514.
(a) Gogoi, S.; Zhao, C.-G. Tetrahedron Lett. 2009, 50, 2252.
(b) Xie, J.; Xing, X.-Y.; Sha, F.; Wu, Z.-Y.; Wu, X.-Y. Org. Biomol. Chem. 2016, 14, 8346.
(a) Liao, Y.-H.; Chen, W.-B.; Wu, Z.-J.; Du, X.-L.; Cun, L.-F.; Zhang, X.-M.; Yuan, W.-C. Adv. Synth. Catal. 2010, 352, 827.
(b) Li, F.; Sun, L.; Teng, Y.; Yu, P.; Zhao, J. C.-G.; Ma, J.-A. Chem.- Eur. J. 2012, 18, 14255.
(c) Li, J.-H.; Du, D.-M. Org. Biomol. Chem. 2015, 13, 5636.
(d) Hack, D.; Chauhan, P.; Deckers, K.; Mizutani, Y.; Raabea, G.; Enders, D. Chem. Commun. 2015, 51, 2266.
(e) Amireddy, M.; Chen, K. RSC Adv. 2016, 6, 77474.
(f) Zheng, Y.; Cui, L.; Wang, Y.; Zhou, Z. J. Org. Chem. 2016, 81, 4340.
(g) Li, J.-H.; Cui, Z.-H.; Du, D.-M. Org. Chem. Front. 2016, 3, 1087.
(h) Hack, D.; Dürr, A. B.; Deckers, K.; Chauhan, P.; Seling, N.; Rübenach, L.; Mertens, L.; Raabe, G.; Schoenebeck, F.; Enders, D. Angew. Chem., Int. Ed. 2016, 55, 1797.
(i) Sharma, V.; Kaur, J.; Chimni, S. S. Eur. J. Org. Chem. 2018, 3489.
(j) Phelan, J. P.; Ellman, J. A. Adv. Synth. Catal. 2016, 358, 1713.
(k) Li, F.; Pei, W.; Wang, J.; Liu, J.; Wang, J.; Zhang, M.-L.; Chen, Z.; Liu, L. Org. Chem. Front. 2018, 5, 1342.
(l) Vila, C.; Slack, S.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2019, 361, 1902.
(m) Rao, K. S.; Ramesh, P.; Trivedi, R.; Kantam, M. L. Tetrahedron Lett. 2016, 57, 1227.
(a) Bao, X.; Wang, B.; Cui, L.; Zhu, G.; He, Y.; Qu, J.; Song, Y. Org. Lett. 2015, 17, 5168.
(b) Amr, F. I.; Vila, C.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Adv. Synth. Catal. 2016, 358, 1583.
(c) Vila, C.; Amr, F. I.; Blay, G.; Muñoz, M. C.; Pedro, J. R. Chem.- Asian J. 2016, 11, 1532.
Yuan, H.; Li, Y.; Zhao, H.; Yang, Z.; Li, X.; Li, W. Chem. Commun. 2019, 55, 12715.
doi: 10.1039/C9CC06360A
Zhou, J.; Huang, W.-J.; Jiang, G.-F. Org. Lett. 2018, 20, 1158.
doi: 10.1021/acs.orglett.8b00025
(a) Yang, L.-C.; Rong, Z.-Q.; Wang, Y.-N.; Tan, Z. Y.; Wang, M.; Zhao, Y. Angew. Chem., Int. Ed. 2017, 56, 2927.
(b) Rong, Z.-Q.; Yang, L.-C.; Liu, S.; Yu, Z.; Wang, Y.-N.; Tan, Z. Y.; Huang, R.-Z.; Lan, Y.; Zhao, Y. J. Am. Chem. Soc. 2017, 139, 15304.
(c) Wang, Y.-N.; Yang, L.-C.; Rong, Z.-Q.; Liu, T.-L.; Liu, R.; Zhao, Y. Angew. Chem., Int. Ed. 2018, 57, 1596.
(d) Qi, J.; Tang, H.; Chen, C.; Cui, S.; Xu, G. Org. Chem. Front. 2019, 6, 2760.
(e) Liu, Y.-Z.; Wang, Z.; Huang, Z.; Zheng, X.; Yang, W.-L.; Deng, W.-P. Angew. Chem., Int. Ed. 2020, 59, 1238.
(f) Xie, H.-P.; Sun, L.; Wu, B.; Zhou, Y.-G. J. Org. Chem. 2019, 84, 15498.
(g) Kuamri, P.; Liu, W.; Wang, C.-J.; Dai, J.; Wang, M.-X.; Yang, Q.-Q.; Deng, Y.-H.; Shao, Z.-H. Chin. J. Chem. 2020, 38, 511.
(h) Trost, B. M.; Zuo, Z. Angew. Chem., Int. Ed. 2020, 59, 1243.
(a) Rong, Z.-Q.; Wang, M.; Chow, C. H. E.; Zhao, Y. Chem.-Eur. J. 2016, 22, 9483.
(b) Ni, H.; Tang, X.; Yao, W.; Ullah, N.; Lu, Y. Angew. Chem., Int. Ed. 2017, 56, 14222.
(c) Chen, J.; Huang, Y. Org. Lett. 2017, 19, 5609.
(a) Gao, Z.-H.; Chen, K.-Q.; Zhang, Y.; Kong, L.-M.; Li, Y.; Ye, S. J. Org. Chem. 2018, 83, 15225.
(b) Chen, K.-Q.; Gao, Z.-H.; Ye, S. Org. Chem. Front. 2019, 6, 405.
Xie, H.-P.; Wu, B.; Wang, X.-W.; Zhou, Y.-G. Chin. J. Catal. 2019, 40, 1566.
doi: 10.1016/S1872-2067(19)63396-6
(a) Chen, J.; Jia, P.; Huang, Y. Org. Lett. 2018, 20, 6715.
(b) Zeng, R.; Shan, C.; Liu, M.; Jiang, K.; Ye, Y.; Liu, T.-Y.; Chen, Y.-C. Org. Lett. 2019, 21, 2312.
(c) Marques, A.-S.; Duhail, T.; Marrot, J.; Chataigner, I.; Coeffard, V.; Vincent, G.; Moreau, X. Angew. Chem., Int. Ed. 2019, 58, 9969.
(a) Gu, Z.; Zhou, J.; Jiang, G.-F.; Zhou, Y.-G. Org. Chem. Front. 2018, 5, 1148.
(b) Gu, Z.; Xie, J.-J.; Jiang, G.-F.; Zhou, Y.-G. Asian J. Org. Chem. 2018, 7, 1561.
(c) Lin, W.; Zhang, C.; Xu, W.; Cheng, Y.; Li, P.; Li, W. Adv. Synth. Catal. 2019, 361, 476.
(d) Lin, W.; Lin, X.; Cheng, Y.; Chang, X.; Zhou, S.; Li, P.; Li, W. Org. Chem. Front. 2019, 6, 2452.
(e) Gu, Z.; Wu, B.; Jiang, G.-F.; Zhou, Y.-G. Chin. J. Chem. 2018, 36, 1130.
(f) Wang, C.-S.; Li, T.-Z.; Cheng, Y.-C.; Zhou, J.; Mei, G.-J.; Shi, F. J. Org. Chem. 2019, 84, 3214.
(g) Li, X.; Yan, J.; Qin, J.; Lin, S.; Chen, W.; Zhan, R.; Huang, H. J. Org. Chem. 2019, 84, 8035.
(h) Fan, T.; Zhang, Z.-J.; Zhang, Y.-C.; Song, J. Org. Lett. 2019, 21, 7897.
(i) Wang, C.-J.; Yang, Q.-Q.; Wang, M.-X.; Shang, Y.-H.; Tong, X.-Y.; Deng, Y.-H.; Shao, Z. Org. Chem. Front. 2020, 7, 609.
Yan, Z.; Gao, X.; Zhou, Y.-G. Chin. J. Catal. 2017, 38, 784.
doi: 10.1016/S1872-2067(17)62804-3
Löser, R.; Chlupacova, M.; Marecek, A.; Opletalova, V.; Gütschow, M. Helv. Chim. Acta 2004, 87, 2597.
doi: 10.1002/hlca.200490232
(a) Ouellet, S. G.; Gauvreau, D.; Cameron, M.; Dolman, S.; Campeau, L.-C.; Hughes, G.; O'Shea, P. D.; Davies, I. W. Org. Process Res. Dev. 2012, 16, 214.
(b) Tsou, H.-R.; MacEwan, G.; Birnberg, G.; Zhang, N.; Brooijmans, N.; Barza, L. T.; Hollander, I.; Kaloustian, S. A.; Yu, K. Bioorg. Med. Chem. Lett. 2010, 20, 2259.
(a) Wang, X.-J.; Tan, J.; Grozinger, K. Tetrahedron Lett. 2000, 41, 4713.
(b) Braňa, M. F.; Gradillas, A.; Ovalles, A. G.; López, B.; Acero, N.; Llinares, F.; Mingarro, D. M. Bioorg. Med. Chem. 2006, 14, 9.
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
.
CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
. CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Yunhao Zhang , Yinuo Wang , Siran Wang , Dazhen Xu . Progress in Selective Construction of Functional Aromatics from Nitrogenous Cycloalkanes. University Chemistry, 2024, 39(11): 136-145. doi: 10.3866/PKU.DXHX202401083
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
Xinxin YU , Yongxing LIU , Xiaohong YI , Miao CHANG , Fei WANG , Peng WANG , Chongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
Jun Huang , Pengfei Nie , Yongchao Lu , Jiayang Li , Yiwen Wang , Jianyun Liu . Efficient adsorption of hardness ions by a mordenite-loaded, nitrogen-doped porous carbon nanofiber cathode in capacitive deionization. Acta Physico-Chimica Sinica, 2025, 41(7): 100066-. doi: 10.1016/j.actphy.2025.100066
Yu Wang , Haiyang Shi , Zihan Chen , Feng Chen , Ping Wang , Xuefei Wang . Hollow AgPt@Pt core-shell cocatalyst with electron-rich Ptδ- shell for boosting selectivity of photocatalytic H2O2 production for faceted BiVO4. Acta Physico-Chimica Sinica, 2025, 41(7): 100081-. doi: 10.1016/j.actphy.2025.100081
Baitong Wei , Jinxin Guo , Xigong Liu , Rongxiu Zhu , Lei Liu . Theoretical Study on the Structure, Stability of Hydrocarbon Free Radicals and Selectivity of Alkane Chlorination Reaction. University Chemistry, 2025, 40(3): 402-407. doi: 10.12461/PKU.DXHX202406003
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Peng YUE , Liyao SHI , Jinglei CUI , Huirong ZHANG , Yanxia GUO . Effects of Ce and Mn promoters on the selective oxidation of ammonia over V2O5/TiO2 catalyst. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 293-307. doi: 10.11862/CJIC.20240210
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016