Citation: Zinatossadat Hossaini, Faramarz Rostami-Charati, Samereh Seyfi, Mehdi Ghambarian. Multicomponent reactions for the synthesis of functionalized 1, 4-oxathiane-3-thiones under microwave irradiation in water[J]. Chinese Chemical Letters, ;2013, 24(05): 376-378.
-
A series of substituted 1,4-oxathiane-3-thione derivatives were synthesized via one-pot multicomponent reactions of nitromethane, carbon disulfide and oxiranes in the presence of Et3N in water as the solvent under microwave irradiation. Particularly valuable features of this method include high yields of products, broad substrate scope, short reaction time and straightforward procedure.
-
-
[1]
[1] M.J. Cook, in: A.R. Katrizky, C.W. Rees (Eds.), Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, 1984, p. 3.
-
[2]
[2] A.H. Haubein, New organophosphorus derivatives of p-thioxane and 2,6-dimethylp-thioxane with insecticidal and acaricidal activity, J. Am. Chem. Soc. 81 (1959) 144-148.
-
[3]
[3] G. Borkow, J. Barnard, T.M. Nguyen, et al., Chemical barriers to human immunodeficiency virus type 1 (HIV-1) infection: retrovirucidal activity of UC781, a thiocarboxanilide nonnucleoside inhibitor of HIV-1 reverse transcriptase, J. Virol. 71 (1997) 3023-3030.
-
[4]
[4] H. Miyauchi, T. Tanio, N. Ohashi, Synthesis and antifungal activity of new azole derivatives containing an oxathiane ring, Bioorg. Med. Chem. Lett. 6 (1996) 2377-2387.
-
[5]
[5] A. Piergentili, W. Quaglia, M. Giannella, Dioxane and oxathiane nuclei: suitable substructures for muscarinic agonists, Bioorg. Med. Chem. 15 (2007) 886-896.
-
[6]
[6] (a) R.E. Parker, N.S. Isaacs, Mechanisms of epoxide reactions, Chem. Rev. 59 (1959) 737-799;
-
[7]
(b) J.G. Buchanan, H.Z. Sable, in: B.S. Thyagarajan (Ed.), Selective Organic Transformations, Wiley-Interscience, New York, 1972;
-
[8]
(c) A.S. Rao, S.K. Paknikar, J.G. Kirtane, Recent advances in the preparation and synthetic applications of oxiranes, Tetrahedron 39 (1983) 2323-2367;
-
[9]
(d) J.G. Smith, Synthetically useful reactions of epoxides, Synthesis 1984 (1984) 629-656.
-
[10]
[7] (a) K.B. Sharpless, The discovery of the asymmetric epoxidation, Chem. Br. 22 (1986) 38-44;
-
[11]
(b) A. Pfenninger, Asymmetric epoxidation of allylic alcohols: the sharpless epoxidation, Synthesis 1986 (1986) 89-116;
-
[12]
(c) R.M. Hanson, The synthetic methodology of nonracemic glycidol and related 2,3-epoxy alcohols, Chem. Rev. 91 (1991) 437-475.
-
[13]
[8] (a) R. Patel, V.P. Srivastava, L.D.S. Yadav, Epoxides to α-mercapto-γ-lactones via ionic liquid promoted mercaptoacetylative ring-opening-ring-closing cascade, Synlett 2010 (2010) 1797-1802;
-
[14]
(b) H.S. Park, D.W. Kwon, K. Lee, Y.H. Kim, A novel synthesis of γ-lactones by tandem epoxide opening-cyclization reaction mediated by samarium(Ⅱ) diiodide, Tetrahedron Lett. 49 (2008) 1616-1618;
-
[15]
(c) S. Antoniotti, E. Dunach, Tin(Ⅳ) triflimidate-catalyzed cyclization of epoxy esters to functionalized d-hydroxy-c-lactones, Tetrahedron Lett. 50 (2009) 2536-2539.
-
[16]
[9] I. Yavari, M. Ghazanfarpour-Darjani, Y. Solgi, S. Ahmadian, Triethylamine-catalyzed efficient synthesis of oxathiolanes containing a highly polarized carbon-carbon double bond from reaction of malononitrile, carbon disulfide (CS2), and oxiranes, Helv. Chim. Acta 94 (2011) 639-642.
-
[1]
-
-
[1]
Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
-
[2]
Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
-
[3]
Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
-
[4]
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
-
[5]
Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
-
[6]
Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
-
[7]
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
-
[8]
Ping Wang , Ting Wang , Ming Xu , Ze Gao , Hongyu Li , Bowen Li , Yuqi Wang , Chaoqun Qu , Ming Feng . Keplerate polyoxomolybdate nanoball mediated controllable preparation of metal-doped molybdenum disulfide for electrocatalytic hydrogen evolution in acidic and alkaline media. Chinese Chemical Letters, 2024, 35(7): 108930-. doi: 10.1016/j.cclet.2023.108930
-
[9]
Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
-
[10]
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
-
[11]
Shaoming Dong , Yiming Niu , Yinghui Pu , Yongzhao Wang , Bingsen Zhang . Subsurface carbon modification of Ni-Ga for improved selectivity in acetylene hydrogenation reaction. Chinese Chemical Letters, 2024, 35(12): 109525-. doi: 10.1016/j.cclet.2024.109525
-
[12]
Yi Zhou , Yanzhen Liu , Yani Yan , Zonglin Yi , Yongfeng Li , Cheng-Meng Chen . Enhanced oxygen reduction reaction on La-Fe bimetal in porous N-doped carbon dodecahedra with CNTs wrapping. Chinese Chemical Letters, 2025, 36(1): 109569-. doi: 10.1016/j.cclet.2024.109569
-
[13]
Jin Long , Xingqun Zheng , Bin Wang , Chenzhong Wu , Qingmei Wang , Lishan Peng . Improving the electrocatalytic performances of Pt-based catalysts for oxygen reduction reaction via strong interactions with single-CoN4-rich carbon support. Chinese Chemical Letters, 2024, 35(5): 109354-. doi: 10.1016/j.cclet.2023.109354
-
[14]
Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2024.100199
-
[15]
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
-
[16]
Yifan LIU , Zhan ZHANG , Rongmei ZHU , Ziming QIU , Huan PANG . A three-dimensional flower-like Cu-based composite and its low-temperature calcination derivatives for efficient oxygen evolution reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 979-990. doi: 10.11862/CJIC.20240008
-
[17]
Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
-
[18]
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
-
[19]
Daheng Wen , Weiwei Fang , Yongmei Liu , Tao Tu . Valorization of carbon dioxide with alcohols. Chinese Chemical Letters, 2024, 35(7): 109394-. doi: 10.1016/j.cclet.2023.109394
-
[20]
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
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(605)
- HTML views(13)