Rapid and Efficient Ultrasound-Assisted Method for the Synthesis of 2-Thioxo-2H-thiopyran and 2-Amino-6-thioxodihydropyridine Derivatives
- Corresponding author: Shi Daqing, dqshi@suda.edu.cn
Citation:
Lin Wei, Zheng Yongxiang, Huang Zhibin, Shi Daqing. Rapid and Efficient Ultrasound-Assisted Method for the Synthesis of 2-Thioxo-2H-thiopyran and 2-Amino-6-thioxodihydropyridine Derivatives[J]. Chinese Journal of Organic Chemistry,
;2017, 37(2): 508-513.
doi:
10.6023/cjoc201608017
Krauze, A.; Germane, S.; Eberlins, O. Eur. J. Med. Chem. 1999, 34, 301.
doi: 10.1016/S0223-5234(99)80081-6
(a) Brown, M. J.; Carter, P. S.; Fenwick, A. E.; Fosberry, A. P.; Hamprecht, D. W.; Hibbs, M. J.; Jarvest, R. L.; Mensah, L.; Milner, P. H.; O'Hanlon, P. J.; Pope, A. J.; Richardson, C. M.; West, A.; Witty, D. R. Bioorg. Med. Chem. Lett. 2002, 12, 3171.
(b) Quaglia, W.; Pigini, M.; Piergentili, A.; Giannella, M.; Gentili, F.; Marucci, G.; Carrieri, A.; Carotti, A.; Poggesi, E.; Leonardi, A.; Melchiorre, C. J. Med. Chem. 2002, 45, 1633.
(c) Sugita, Y.; Hosoya, H.; Terasawa, K.; Yokoe, I.; Fujisawa, S.; Sakagami, H. Anticancer Res. 2001, 21, 2629.
Freifeld, L.; Shojael, H.; Langer, P. J. Org. Chem. 2006, 71, 4965.
doi: 10.1021/jo060593h
Eynde, J. J.; Defosse, F.; Mayence, A.; Haverbeke, Y. V. Tetrahedron 1995, 51, 6511.
doi: 10.1016/0040-4020(95)00318-3
Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2003, 44, 4129.
doi: 10.1016/S0040-4039(03)00813-X
(a) Abbas, A. E.; Rahele, H. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 2267.
(b) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
(c) Jagodziński, T. S.; Sośnicki, J. G.; Wesolowska, A. Tetrahedron 2003, 59, 4183.
(d) Rios, R.; Sundén, H.; Ibrahem, L.; Zhao, G. L.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8547.
(e) Krystyna, B. S.; Malgorzata, K. Monatsh. Chem. 2006, 137, 347.
(a) Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.
(b) Ji, S. J.; Shi, D. Q. New Technology of Modern Organic Synthesis, Chemical Industry Press, Bejing, 2009 (in Chinese).(纪顺俊, 史达清, 现代有机合成新技术, 化学工业出版社, 北京, 2009.)
(c) Li, J. T.; Wang, S. X.; Chen, G. F.; Li, T. S. Curr. Org. Synth. 2005, 2, 425.
(a) Wolfe, S.; Ingold, C. F. J. Am. Chem. Soc. 1983, 105, 7755.
(b) Peng, K.; Chen, F. X.; She, X. G.; Yang, C. H.; Cui, Y. X.; Pan, X. F. Tetrahedron Lett. 2005, 46, 1217.
(a) Suslick, K. S.; Casadonate, D. J. Am. Chem. Soc. 1987, 109, 3459.
(b) Pasha, M. A.; Jayashankara, V. P. Ultrason. Sonochem. 2005, 12, 433.
(a) Hofmann, J.; Freier, U.; Weeks, M. Ultrason. Sonochem. 2003, 10, 271.
(b) Meciarova, M.; Kiripolsky, M.; Toma, S. Ultrason. Sonochem. 2005, 12, 401.
(c) Martins, M. A. P.; Rossatto, M.; Prola, L. D. T.; Pizzuti, L.; Moreira, D. N.; Campos, P. T.; Frizzo, C. P.; Zanatta, N.; Bonacorso, H. G. Ultrason. Sonochem. 2012, 19, 227.
Li, J. T.; Chen, G. F.; Xu, W. Z.; Li, T. S. Ultrason. Sonochem. 2003, 10, 115.
doi: 10.1016/S1350-4177(02)00134-7
(a) Li, J. T.; Yang, W. Z.; Wang, S. X.; Li, S. H.; Li, T. S. Ultrason. Sonochem. 2001, 4, 55.
(b) Zhang, Z. H.; Li, J. T.; Li, T. S. Ultrason. Sonochem. 2008, 15, 673.
(a) Zhang, J.; Yang, F.; Ren, G.; Mark, T. C. W.; Song, M.; Wu, Y. Ultrason. Sonochem. 2008, 15, 115.
(b) Polackova, V.; Hutka, M.; Toma, S. Ultrason. Sonochem. 2005, 12, 99.
(a) Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H. L.; Shi, D. Q. Ultrason. Sonochem. 2011, 18, 708.
(b) Zou, Y.; Hu, Y.; Liu, H.; Shi, D. Q. ACS Comb. Sci. 2012, 14, 38.
(c) Hu, Y.; Zou, Y.; Wu, H.; Shi, D. Q. Ultrason. Sonochem. 2012, 19, 264.
(d) Yang, J. M.; Li, Q.; Zhang, J. J.; Lin, W.; Wang, J. X.; Wang, Y. C.; Huang, Z. B.; Shi, D. Q. Molecules 2013, 18, 14519.
(e) Liu, H.; Zou, Y.; Hu, Y.; Shi, D. Q. J. Heterocycl. Chem. 2011, 48, 877.
(f) Shi, D. Q.; Zou, Y.; Hu, Y.; Wu, H. J. Heterocycl. Chem. 2011, 48, 896.
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H2O2合成:协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
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
Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
Hong CAI , Jiewen WU , Jingyun LI , Lixian CHEN , Siqi XIAO , Dan LI . Synthesis of a zinc-cobalt bimetallic adenine metal-organic framework for the recognition of sulfur-containing amino acids. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 114-122. doi: 10.11862/CJIC.20240382
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
Aiyi Xin , Jiawei Li , Xinyang Ran , Chuanjiang Fu , Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031
Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
Xiaofang Li , Zhigang Wang . Modulating dz2-orbital occupancy of Au cocatalysts for enhanced photocatalytic H2O2 production. Acta Physico-Chimica Sinica, 2025, 41(7): 100080-. doi: 10.1016/j.actphy.2025.100080
Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
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
Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
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
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
Ziliang KANG , Jiamin ZHANG , Hong AN , Xiaohua LIU , Yang CHEN , Jinping LI , Libo LI . Preparation and water adsorption properties of CaCl2@MOF-808 in-situ composite moulded particles. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2133-2140. doi: 10.11862/CJIC.20240282