K2S2O8-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines
- Corresponding author: Zhou Shufeng, szhou@hqu.edu.cn Cui Xiuling, cuixl@hqu.edu.cn
Citation:
Chen Zhichao, Zhang Hong, Zhou Shufeng, Cui Xiuling. K2S2O8-Initiated Cascade Cyclization of 2-Alkynylnitriles with Sodium Sulfinates: Access to Fused Cyclopenta[gh]phenanthridines[J]. Chinese Journal of Organic Chemistry,
;2020, 40(11): 3866-3872.
doi:
10.6023/cjoc202007005
(a) Günes, H. S.; Gözler, B. Fitoterapia 2001, 72, 875.
(b) Wang, X.-L.; Liu, B.-R.; Chen, C.-K.; Wang, J.-R.; Lee, S.-S. Fitoterapia 2011, 82, 793.
(c) Belkis, G.; Alan, J. F.; Maurice, S. J. Nat. Prod. 1990, 53, 675.
(d) Fajardo, V.; Araya, M.; Cuadra, P.; Oyarzun, A.; Gallardo, A.; Cueto, M.; Joseph-Nathan, P. J. Nat. Prod. 2009, 72, 1355.
(e) Honda, T.; Shigehisa, H. Org. Lett. 2006, 8, 657.
(f) Khunnawutmanotham, N.; Sahakitpichan, P.; Chimnoi, N.; Techasakul, S. Eur. J. Org. Chem. 2015, 28, 6324.
Párraga, J.; Galán, A.; Sanz, M. J.; Cabedo, N.; Cortes, D. Eur. J. Med. Chem. 2015, 90, 101.
doi: 10.1016/j.ejmech.2014.11.009
(a) Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G. Tetrahedron Lett. 1998, 39, 2441.
(b) Chowdhury, S.; Zhao, B.; Snieckus, V. Polycyclic Aromat. Compd. 1995, 5, 27.
(c) Wu, Y.; Wong, S. M.; Mao, F.; Chan, T. L.; Kwong, F. Y. Org. Lett. 2012, 14, 5306.
(a) Sciabola, S.; Carosati, E.; Baroni, M.; Mannhol, R. J. Med. Chem. 2005, 48, 3756.
(b) Tfelt-Hansen, P.; De Vries, P.; Saxena, P. R. Drugs 2000, 60, 1259.
(c) Artico, M.; Silvestri, R.; Massa, S.; Loi, A. G.; Corrias, S.; Piras, G.; Colla, P. L. J. Med. Chem. 1996, 39, 522.
(d) Harrak, Y.; Casula, G.; Basset, J.; Rosell, G.; Plescia, S.; Raffa, D.; Cusimano, M. G.; Pouplana, R.; Pujol, M. D. J. Med. Chem. 2010, 53, 6560.
(e) Emmett, E. J.; Hayter, B. R.; Willis, M. C. Angew. Chem., Int. Ed. 2014, 53, 10204.
(a) Wu, Z.; Song, H.; Cui, X.; Pi, C.; Du, W.; Wu, Y. Org. Lett. 2013, 15, 1270.
(b) Mi, X.; Kong, Y.; Zhang, J.; Pi, C.; Cui, X. Chin. Chem. Lett. 2019, 30, 2295.
(c) Zhang, Z.; Yan, J.; Ma, D.; Sun, J. Chin. Chem. Lett. 2019, 30, 1509.
(d) Peng, S.; Song, Y.-X.; He, J.-Y.; Tang, S.-S.; Tan, J.-X.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2287.
(e) Yu, H.; Pi, C.; Wang, Y.; Cui, X.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 124(in Chinese).
(余海洋, 皮超, 王勇, 崔秀灵, 吴养洁, 有机化学, 2018, 38, 124.)
(f) Shi, Z.-J.; Wang, L.-H.; Cui, X. Chin. J. Org. Chem. 2019, 39, 1596(in Chinese).
(施兆江, 王连会, 崔秀灵, 有机化学, 2019, 39, 1596.)
(g) Xie, L.-Y.; Fang, T.-G.; Tan, J.-X.; Zhang, B.; Cao, Z.; Yang, L.-H.; He, W.-M. Green Chem. 2019, 21, 3858.
(h) Xie, L.-Y.; Peng, S.; Tan, J.-X.; Sun, R.-X.; Yu, X.; Dai, N.-N.; He, W.-M. ACS Sustainable Chem. Eng. 2018, 6, 16976.
(i) Xie, L.-Y.; Li, Y.-J.; Qu, J.; Duan, Y.; Hu, J.; Liu, K.-J.; Cao, Z.; He, W.-M. Green Chem. 2017, 19, 5642.
(j) Cao, Z.; Zhu, Q.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2132.
(a) Shaabani, A.; Mirzaei, P.; Naderi, S.; Lee, D. G. Tetrahedron 2004, 60, 11415.
(b) Kozak, J. A.; Dake, G. R. Angew. Chem., Int. Ed. 2008, 47, 4221.
(c) Pritzius, A. B.; Breit, B. Angew. Chem., Int. Ed. 2015, 54, 3121.
(a) Olah, G. A.; Kobayashi, S.; Nishimura, J. J. Am. Chem. Soc. 1973, 95, 564.
(b) Répichet, S.; Le Roux, C.; Hernandez, P.; Dubac, J.; Desmurs, J.-R. J. Org. Chem. 1999, 64, 6479.
(c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Parisi, L. M. Org. Lett. 2002, 4, 4719.
(d) Baskin, J. M.; Wang, Z. Org. Lett. 2002, 4, 4423.
(a) Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2004, 356, 2029.
(b) Tang, X.; Huang, L.; Xu, Y.; Yang, J.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed. 2014, 53, 4205.
(c) Xu, Y.; Tang, X.; Hu, W.; Wu, W.; Jiang, H. Green Chem. 2014, 16, 3720.
(d) Wu, W.-Q.; Yi, S.; Yu, Y.; Huang, W.; Jiang, H.-F. J. Org. Chem. 2017, 82, 1224.
(a) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134.
(b) Grondal, C.; Jeanty, M.; Enders, D. Nat. Chem. 2010, 2, 167.
(c) Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278.
(d) Volla, C. M. R.; Atodiresei, I.; Rueping, M. Chem. Rev. 2014, 114, 2390.
(e) Wang, Y.; Lu, H.; Xu, P.-F. Acc. Chem. Res. 2015, 48, 1832.
(f) Xuan, J.; Studer, A. Chem. Soc. Rev. 2017, 46, 4329.
(g) Zhang, Y.-L.; Sun, K.; Lv, Q.-Y.; Chen, X.-L.; Qu, L.-B.; Yu, B. Chin. Chem. Lett. 2019, 30, 1361.
(h) Ren, L.-J.; Ran, M.-G.; He, J.-X.; Qian, Y.; Yao, Q.-L. Chin. J. Org. Chem. 2019, 39, 1583(in Chinese).
(任林静, 冉茂刚, 何佳芯, 钱燕, 姚秋丽, 有机化学, 2019, 39, 1583.)
(a) Li, X.; Fang, X.; Zhuang, S.; Liu, P.; Sun, P. Org. Lett. 2017, 19, 3580.
(b) Yu, Y.; Cai, Z.; Yuan, W.; Liu, P.; Sun, P. J. Org. Chem. 2017, 82, 8148.
(c) Zhang, C.; Pi, J.; Chen, S.; Liu, P.; Sun, P. Org. Chem. Front. 2018, 5, 793.
(d) Xu, P.; Zhu, Y.-M.; Wang, F.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2019, 21, 683.
(e) Zheng, J.; Zhang, Y.; Wang, D.; Cui, S. Org. Lett. 2016, 18, 1768.
(f) Wu, L.-J.; Yang, Y.; Song, R.-J.; Yu, J.-X.; Li, J.-H.; He, D.-L. Chem. Commun. 2018, 54, 1367.
(g) Liu, X.; Wu, Z.; Zhang, Z.; Liu, P.; Sun, P. Org. Biomol. Chem. 2018, 16, 414.
(h) Shang, J.-Q.; Wang, S.-S.; Fu, H.; Li, Y.; Yang, T.; Li, Y.-M. Org. Chem. Front. 2018, 5, 1945.
(a) Zhou, B.; Chen, W.; Yang, Y.; Yang, Y.; Deng, G.; Liang, Y. Org. Biomol. Chem. 2018, 16, 7959.
(b) Xie, L.-Y.; Peng, S.; Liu, F.; Chen, G.-R.; Xia, W.; Yu, X.; He, W.-M. Org. Chem. Front. 2018, 5, 2604.
(c) Wu, W.-Q.; Yi, S.-J.; Huang, W.; Luo, D.; Jiang, H.-F. Org. Lett. 2017, 19, 2825.
(d) Wei, W.; Wen, J.-W.; Yang, D.-S.; Du, J.; You, J.-M.; Wang, H. Green Chem. 2014, 16, 2988.
(e) Gao, M.; Li, Y.; Xie, L.; Chauvin, R.; Cui, X. Chem. Commun. 2016, 52, 2846.
Zhou, N.-N.; Wu, M.-X.; Zhang, M.; Zhou, X.-Q.; Zhou, W. Org. Biomol. Chem. 2020, 18, 1733.
doi: 10.1039/D0OB00119H
Binyang Qin , Mengqi Wang , Shimei Wu , Yining Li , Chilin Liu , Yufei Zhang , Haosen Fan . Carbon dots confined nanosheets assembled NiCo2S4@CDs cross-stacked architecture for enhanced sodium ion storage. Chinese Chemical Letters, 2024, 35(7): 108921-. doi: 10.1016/j.cclet.2023.108921
Ruofan Yin , Zhaoxin Guo , Rui Liu , Xian-Sen Tao . Ultrafast synthesis of Na3V2(PO4)3 cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643
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
Jing-Qi Tao , Shuai Liu , Tian-Yu Zhang , Hong Xin , Xu Yang , Xin-Hua Duan , Li-Na Guo . Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade. Chinese Chemical Letters, 2024, 35(6): 109263-. doi: 10.1016/j.cclet.2023.109263
Chonglong He , Yulong Wang , Quan-Xin Li , Zichen Yan , Keyuan Zhang , Shao-Fei Ni , Xin-Hua Duan , Le Liu . Alkylarylation of alkenes with arylsulfonylacetate as bifunctional reagent via photoredox radical addition/Smiles rearrangement cascade. Chinese Chemical Letters, 2025, 36(5): 110253-. doi: 10.1016/j.cclet.2024.110253
Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe2O4@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971
Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
Xuan Wang , Peng Sun , Siteng Yuan , Lu Yue , Yufeng Zhao . P2-type low-cost and moisture-stable cathode for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(5): 110015-. doi: 10.1016/j.cclet.2024.110015
Yanxue Wu , Xijun Xu , Shanshan Shi , Fangkun Li , Shaomin Ji , Jingwei Zhao , Jun Liu , Yanping Huo . Facile construction of Cu2-xSe@C nanobelts as anode for superior sodium-ion storage. Chinese Chemical Letters, 2025, 36(6): 110062-. doi: 10.1016/j.cclet.2024.110062
Luyan Shi , Ke Zhu , Yuting Yang , Qinrui Liang , Qimin Peng , Shuqing Zhou , Tayirjan Taylor Isimjan , Xiulin Yang . Phytic acid-derivative Co2B-CoPOx coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222
Dongmei Dai , Xiaobing Lai , Xiaojuan Wang , Yunting Yao , Mengmin Jia , Liang Wang , Pengyao Yan , Yaru Qiao , Zhuangzhuang Zhang , Bao Li , Dai-Huo Liu . Increasing (010) active plane of P2-type layered cathodes with hexagonal prism towards improved sodium-storage. Chinese Chemical Letters, 2024, 35(10): 109405-. doi: 10.1016/j.cclet.2023.109405
Huixin Chen , Chen Zhao , Hongjun Yue , Guiming Zhong , Xiang Han , Liang Yin , Ding Chen . Unraveling the reaction mechanism of high reversible capacity CuP2/C anode with native oxidation POx component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650
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
Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO2F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
Guangchang Yang , Shenglong Yang , Jinlian Yu , Yishun Xie , Chunlei Tan , Feiyan Lai , Qianqian Jin , Hongqiang Wang , Xiaohui Zhang . Regulating local chemical environment in O3-type layered sodium oxides by dual-site Mg2+/B3+ substitution achieves durable and high-rate cathode. Chinese Chemical Letters, 2024, 35(9): 109722-. doi: 10.1016/j.cclet.2024.109722
Jun Dong , Senyuan Tan , Sunbin Yang , Yalong Jiang , Ruxing Wang , Jian Ao , Zilun Chen , Chaohai Zhang , Qinyou An , Xiaoxing Zhang . Spatial confinement of free-standing graphene sponge enables excellent stability of conversion-type Fe2O3 anode for sodium storage. Chinese Chemical Letters, 2025, 36(3): 110010-. doi: 10.1016/j.cclet.2024.110010
Jingtai Bi , Yupeng Cheng , Mengmeng Sun , Xiaofu Guo , Shizhao Wang , Yingying Zhao . Efficient and selective photocatalytic nitrite reduction to N2 through CO2 anion radical by eco-friendly tartaric acid activation. Chinese Chemical Letters, 2024, 35(11): 109639-. doi: 10.1016/j.cclet.2024.109639
Hui Wang , Haodong Ji , Dandan Zhang , Xudong Yang , Hanchun Chen , Chunqian Jiang , Weiliang Sun , Jun Duan , Wen Liu . Solar-light-driven photocatalytic degradation and detoxification of ciprofloxacin using sodium niobate nanocubes decorated g-C3N4 with built-in electric field. Chinese Chemical Letters, 2025, 36(5): 110200-. doi: 10.1016/j.cclet.2024.110200
Tao Long , Peng Chen , Bin Feng , Caili Yang , Kairong Wang , Yulei Wang , Can Chen , Yaping Wang , Ruotong Li , Meng Wu , Minhuan Lan , Wei Kong Pang , Jian-Fang Wu , Yuan-Li Ding . Reinforced concrete-like Na3.5V1.5Mn0.5(PO4)3@graphene hybrids with hierarchical porosity as durable and high-rate sodium-ion battery cathode. Chinese Chemical Letters, 2024, 35(4): 109267-. doi: 10.1016/j.cclet.2023.109267