Alkali Salt-Catalyzed Aza-Michael Addition of 1, 2, 4-Triazole to α, β-Unsaturated Ketones and Imides
- Corresponding author: Ma Ben, maben@nwnu.edu.cn Yang Jingya, yangjy@nwnu.edu.cn
Citation:
Ma Ben, Wang Ganggang, Zhou Hongyan, Yang Jingya. Alkali Salt-Catalyzed Aza-Michael Addition of 1, 2, 4-Triazole to α, β-Unsaturated Ketones and Imides[J]. Chinese Journal of Organic Chemistry,
;2020, 40(1): 115-124.
doi:
10.6023/cjoc201907050
(a) Zheng, K.; Liu, X.; Feng, X. Chem. Rev. 2018, 118, 7586.
(b) Gmach, J.; Błażewska, K. M. Synthesis 2016, 48, 2681.
(c) Sánchez-Roselló, M.; Aceña, J. L.; Simón-Fuentes, A.; del Pozo, C. Chem. Soc. Rev. 2014, 43, 7430.
(d) Amara, Z.; Caron, J.; Joseph, D. Nat. Prod. Rep. 2013, 30, 1211.
(e) Wang, J.; Li, P.; Choy, P. Y.; Chan, A. S. C.; Kwong, F. Y. ChemCatChem 2012, 4, 917.
(f) Enders, D.; Wang, C.; Liebich, J. X. Chem. Eur. J. 2009, 15, 11058.
(g) Xu, L. W.; Xia, C. G. Eur. J. Org. Chem. 2005, 633.
(a) Roy, T. K.; Parhi, B.; Ghorai, P. Angew. Chem., Int. Ed. 2018, 57, 9397.
(b) Barát, V.; Csókás, D.; Bates, R. W. J. Org. Chem. 2018, 83, 9088.
(c) Wu, L.; Jin, R.; Li, L.; Hu, X.; Cheng, T.; Liu, G. Org. Lett. 2017, 19, 3047.
(d) Yang, X.; Chen, Z.; Cai, Y.; Huang, Y. Y.; Shibata, N. Green Chem. 2014, 16, 4530.
(e) Amara, Z.; Caron, J.; Joseph, D. Nat. Prod. Rep. 2013, 30, 1211.
(f) Mikami, K.; Fustero, S.; Sánchez-Roselló, M.; Aceña, J. L.; Soloshonok, V.; Sorochinsky, A. Synthesis 2011, 3045.
(g) Weiner, B.; Szymański, W.; Janssen, D. B.; Minnaard, A. J.; Feringa, B. L. Chem. Soc. Rev. 2010, 39, 1656.
(h) Vinogradov, M. G.; Turovaa, O. V.; Zlotin, S. G. Org. Biomol. Chem. 2019, 17, 3670.
(a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044.
(b) Bartoli, G.; Bosco, M.; Marcantoni, E.; Petrini, M.; Sambri, L.; Torregiani, E. J. Org. Chem. 2001, 66, 9052.
(c) Reboule, I.; Gil, R.; Collin, J. Tetrahedron Lett. 2005, 46, 7761.
(d) Loh, T. P.; Wei, L. L. Synlett 1998, 975.
(e) Wabnitz, T. C.; Spencer, J. B. Tetrahedron Lett. 2002, 43, 3891.
(f) Azizi, N.; Saidi, M. R. Tetrahedron 2004, 60, 383.
(g) Stanley, L. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2009, 48, 7841.
(h) Sukhorukov, A. Y.; Sukhanova, A. A.; Zlotin, S. G. Tetrahedron 2016, 72, 6191.
(a) Gandelman, M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 2393.
(b) Wang, J.; Li, H.; Zu, L.; Wang, W. Org. Lett. 2006, 8, 1391.
(c) Uria, U.; Vicario, J. L.; Badía, D.; Carrillo, L. Chem. Commun. 2007, 2509.
(d) Wang, J.; Zu, L.; Li, H.; Xie, H.; Wang, W. Synthesis 2007, 2576.
(e) Madhavan, N.; Takatani, T.; Sherrill, C. D.; Weck, M. Chem. Eur. J. 2009, 15, 1186.
(f) Luo, G. S.; Zhang, S. L.; Duan, W. H.; Wang, W. Synthesis 2009, 1564.
(g) Lv, J.; Wu, H.; Wang, Y. Eur. J. Org. Chem. 2010, 11, 2073.
(h) Zhou, Y.; Li, X.; Li, W.; Wu, C.; Liang, X.; Ye, J. Synlett 2010, 2357.
(i) Guo, H. M.; Yuan, T. F.; Niu, H. Y.; Liu, J. Y.; Mao, R. Z. D.; Li, Y.; Qu, G. R. Chem. Eur. J. 2011, 17, 4095.
(j) Lee, S. J.; Youn, S. H.; Cho, C. W. Org. Biomol. Chem. 2011, 9, 7734.
(k) Li, H.; Zhao, J.; Zeng, L.; Hu, W. J. Org. Chem. 2011, 76, 8064.
(l) Uria, U.; Reyes, E.; Vicario, J. L.; Badía, D.; Carrillo, L. Org. Lett. 2011, 13, 336.
(m) Wang, J.; Wang, W.; Liu, X.; Hou, Z.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2011, 11, 2039.
(n) Wu, H.; Tian, Z.; Zhang, L.; Huang, Y.; Wang, Y. Adv. Synth. Catal. 2012, 354, 2977.
(o) Lee, S. J.; Ahn, J. G.; Cho, C. W. Tetrahedron: Asymmetry 2014, 25, 1383.
(p) Chen, S. W.; Zhang, G. C.; Lou, Q. X.; Cui, W.; Zhang, S. S.; Hu, W. H.; Zhao, J. L. ChemCatChem 2015, 7, 1935.
(q) Kim, S.; Kang, S.; Kim, G.; Lee, Y. J. Org. Chem. 2016, 81, 4048.
(r) Bhagat, U. K.; Peddinti, R. K. Synlett 2018, 29, 99.
(s) Chittimalla, S. K.; Nakka, S.; Koodalingam, M.; Bandi, C. Synlett 2018, 29, 57.
(t) Bhagat, U. K.; Peddinti, R. K. J. Org. Chem. 2018, 83, 793.
(a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
(b) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
(c) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
(d) Towns, A. D. Dyes Pigm. 1999, 42, 3.
(e) Hughes, G.; Bryce, M. R. J. Mater. Chem. 2005, 15, 94.
(f) Holmes, G.; Rice, A.; Snyder, K. C. R. J. Mater. Sci. 2006, 41, 4105.
(g) Kusama, H.; Sugihara, H.; Sayama, K. J. Phys. Chem. C 2009, 113, 20764.
Ghannoum, M. A.; Rice, L. B. Clin. Microbiol. Rev. 1999, 12, 50.
(a) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
(b) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
(c) Jagerovic, N.; Hernandez-Folgado, L.; Alkorta, I.; Goya, P.; Navarro, M.; Serrano, A.; de Fonseca, F. R.; Dannert, M. T.; Alsasua, A.; Suardiaz, M.; Pascual, D.; Martín, M. I. J. Med. Chem. 2004, 47, 2939.
(d) Papadopoulou, M. V.; Trunz, B. B.; Bloomer, W. D.; McKenzie, C.; Wilkinson, S. R.; Prasittichai, C.; Brun, R.; Kaiser, M.; Torreele, E. J. Med. Chem. 2011, 54, 8214.
(e) Moulin, A.; Demange, L.; Ryan, J.; Mousseaux, D.; Sanchez, P.; Bergé, G.; Gagne, D.; Perrissoud, D.; Locatelli, V.; Torsello, A.; Galleyrand, J. C.; Fehrentz, J. A.; Martinez, J. J. Med. Chem. 2008, 51, 689.
(f) Fustero, S.; Pina, B.; Salavert, E.; Navarro, A.; de Arellano, M. C. R.; Fuentes, A. S. J. Org. Chem. 2002, 67, 4667.
(a) Huntsman, E.; Balsells, J. Eur. J. Org. Chem. 2005, 3761.
(b) Larsen, S. D.; DiPaolo, B. A. Org. Lett. 2001, 3, 3341.
(c) Stocks, M. J.; Cheshire, D. R.; Reynold, R. Org. Lett. 2004, 6, 2969.
(d) Zhang, J. P.; Lin, Y. Y.; Huang, X. C.; Chen, X. M. J. Am. Chem. Soc. 2005, 127, 5495.
(e) Ueda, S.; Nagasawa, H. J. Am. Chem. Soc. 2009, 131, 15080.
(f) Guru, M. M.; Punniyamurthy, T. J. Org. Chem. 2012, 77, 5063.
(g) Tam, A.; Armstrong, I. S.; La Cruz, T. E. Org. Lett. 2013, 15, 3586.
(h) Xu, H.; Ma, S.; Xu, Y.; Bian, L.; Ding, T.; Fang, X.; Zhang, W.; Ren, Y. J. Org. Chem. 2012, 80, 1758.
(i) Huang, H.; Guo, W.; Wu, W.; Li, C.; Jiang, H. Org. Lett. 2015, 17, 2894.
(j) Song, L.; Tian, X.; Lv, Z.; Li, E.; Wu, J.; Liu, Y.; Yu, W.; Chang, J. J. Org. Chem. 2015, 80, 7219.
(k) Chen, Z.; Li, H.; Dong, W.; Miao, M.; Ren, H. Org. Lett. 2016, 18, 1334.
(l) Yu, W.; Huang, Y.; Li, J.; Tang, X.; Wu, W.; Jiang, H. J. Org. Chem. 2018, 83, 9334.
(m) Li, H.; Wu, X.; Hao, W.; Li, H.; Zhao, Y.; Wang, Y.; Lian, P.; Zheng, Y.; Bao, X.; Wan, X. Org. Lett. 2018, 20, 5224.
Liu, B. K.; Wu, Q.; Qian, X. Q.; Lv, D. S.; Lin, X. F. Synthesis 2007, 2653.
Uddin, M. I.; Nakano, K.; Ichikawa, Y.; Kotsuki, H. Synlett 2008, 1402.
Dinér, P.; Nielsen, M.; Marigo, M.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2007, 46, 1983.
doi: 10.1002/anie.200604854
Zhou, Y. F.; Li, X.; Li, W. L.; Wu, C. L.; Liang, X. M.; Ye, J. X. Synlett 2008, 1402.
(a) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442.
(b) Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928.
(c) Madhavan, N.; Weck, M. Adv. Synth. Catal. 2008, 350, 419.
(d) Mazet, C.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1762.
(e) Madhavan, N.; Sommer, W.; Weck, M. J. Mol. Catal. A: Chem. 2011, 334, 1.
Yang, J.; Ma, B.; Zhou, H.; Zhan, B.; Li, Z. Chin. J. Org. Chem. 2015, 35, 121(in Chinese).
Yang, J.; Bao, Y.; Zhou, H.; Li, T.; Li, N.; Li, Z. Synthesis 2016, 48, 1139.
doi: 10.1055/s-0035-1561334
Zhou, H.; Xiang, X.; Ma, B.; Wang, G.; Zhang, Z.; Yang, J. Synthesis 2019, 51, 3142.
doi: 10.1055/s-0037-1611520
Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
Yan Luo , Yan-Jiao Lu , Mei-Mei Pan , Yu-Feng Liang , Wei-Min Shi , Chun-Hua Chen , Cui Liang , Gui-Fa Su , Dong-Liang Mo . Rapidly diastereoselective assembly of ten-membered N-heterocycles between two 1,3-dipoles and their diversity to access fused N-heterocycles. Chinese Chemical Letters, 2025, 36(5): 110207-. doi: 10.1016/j.cclet.2024.110207
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
Lihua HUANG , Jian HUA . Denitration performance of HoCeMn/TiO2 catalysts prepared by co-precipitation and impregnation methods. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 629-645. doi: 10.11862/CJIC.20230315
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
Guihuang Fang , Wei Chen , Hongwei Yang , Haisheng Fang , Chuang Yu , Maoxiang Wu . Improved performance of LiMn0.8Fe0.2PO4 by addition of fluoroethylene carbonate electrolyte additive. Chinese Chemical Letters, 2024, 35(6): 108799-. doi: 10.1016/j.cclet.2023.108799
Zixuan Zhu , Xianjin Shi , Yongfang Rao , Yu Huang . Recent progress of MgO-based materials in CO2 adsorption and conversion: Modification methods, reaction condition, and CO2 hydrogenation. Chinese Chemical Letters, 2024, 35(5): 108954-. doi: 10.1016/j.cclet.2023.108954
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
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
Shehla Khalid , Muhammad Bilal , Nasir Rasool , Muhammad Imran . Photochemical reactions as synthetic tool for pharmaceutical industries. Chinese Chemical Letters, 2024, 35(9): 109498-. doi: 10.1016/j.cclet.2024.109498
Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
Yuxiang Zhang , Jia Zhao , Sen Lin . Nitrogen doping retrofits the coordination environment of copper single-atom catalysts for deep CO2 reduction. Chinese Journal of Structural Chemistry, 2024, 43(11): 100415-100415. doi: 10.1016/j.cjsc.2024.100415
Sushu Zhang , Yang Yang , Jingyu Wang . Pyridinic nitrogen-substituted graphene membranes for exceptional CO2 capture. Chinese Journal of Structural Chemistry, 2025, 44(2): 100440-100440. doi: 10.1016/j.cjsc.2024.100440
Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
Shicheng Dong , Jun Zhu . Could π-aromaticity cross an unsaturated system to a fully saturated one?. Chinese Chemical Letters, 2024, 35(6): 109214-. doi: 10.1016/j.cclet.2023.109214
Yujie Li , Ya-Nan Wang , Yin-Gen Luo , Hongcai Yang , Jinrui Ren , Xiao Li . Advances in synthetic biology-based drug delivery systems for disease treatment. Chinese Chemical Letters, 2024, 35(11): 109576-. doi: 10.1016/j.cclet.2024.109576
Jian Li , Jinjin Chen , Qi-Long Hu , Zhen Wang , Xiao-Feng Xiong . Recent progress of chemical methods for lysine site-selective modification of peptides and proteins. Chinese Chemical Letters, 2025, 36(5): 110126-. doi: 10.1016/j.cclet.2024.110126