水相一锅煮合成1,3,4-噁二唑-5-硫醚类化合物

水相一锅煮合成1,3,4-噁二唑-5-硫醚类化合物

闫旭, 葛泽梅^*, 程铁明, 李润涛^*

北京大学天然药物及仿生药物国家重点实验室; 药学院化学生物学系, 北京 100191

收稿日期:2008-09-15 修回日期:2008-11-10 出版日期:2008-12-15 发布日期:2008-12-15
通讯作者: 李润涛*

One-pot synthesis of 1,3,4-oxadiazole-5-thioethers in water

Xu Yan, Ze-Mei Ge^*, Tie-Ming Cheng, Run-Tao Li^*

The State Key Laboratory of Natural and Biomimetic Drugs;
Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China

Received:2008-09-15 Revised:2008-11-10 Online:2008-12-15 Published:2008-12-15
Contact: Run-Tao Li*

摘要/Abstract

摘要：

此文报道了由酰肼, 二硫化碳及卤代烃或α, β-不饱羰基化合物在水相中一锅煮反应合成1,3,4-噁二唑-5-硫醚类化合物的方法。该方法具有高效、反应条件温和、操作简单、适用范围广和环境友好等优点.

关键词: 1,3,4-噁二唑-5-硫醚, 1,3,4-噁二唑-5-硫醚, 1,3,4-噁二唑-5-硫醚, 一锅煮合成, 一锅煮合成, 一锅煮合成, 环境友好, 环境友好, 环境友好, 水相, 水相, 水相, 酰肼, 酰肼, 酰肼, 磷酸钾, 磷酸钾, 磷酸钾

Abstract: An efficient and environmental-friendly one-pot procedure has been developed for the synthesis of 1,3,4-oxadiazole-5-thioethers by the reaction of acylhydrazine with carbon disulfide and organic halides or α, β-unsaturated carbonyl compounds. The reactions were carried out in water in the presence of potassium phosphate within 2–4 h to afford the expected products in excellent yields.

Key words: 1,3,4-Oxadiazole-5-thioether, 1,3,4-Oxadiazole-5-thioether, One-pot synthesis, One-pot synthesis, Environmental-friendly, Environmental-friendly, Aqueous medium, Aqueous medium, Acylhydrazine, Acylhydrazine, Potassium phosphate, Potassium phosphate

Supporting: Foundation items: Natural Science Foundation of China (Grant No. 20672009) and the Major State Basic Research Development Program (Grant No. 2004CB719900).
^*Corresponding author. Tel.: 010-82801504;

闫旭, 葛泽梅^*, 程铁明, 李润涛^*
. 水相一锅煮合成1,3,4-噁二唑-5-硫醚类化合物
[J]. .

Xu Yan, Ze-Mei Ge^*, Tie-Ming Cheng, Run-Tao Li^*
. One-pot synthesis of 1,3,4-oxadiazole-5-thioethers in water
[J]. .

参考文献

[1] (a) Ali, A.; Omar, A.; Mohamed, A.; Jochen, L. Bioorg. Med. Chem. 2004, 12, 5107-5113. (b) Zareef, M.; Iqbal, R.; Al-Masoudi, N.A.; Zaidi, J.H.; Arfan, M. Heteratom Chem. 2007, 18, 425-431.
[2] Huang, W.; Liu, M.Z.; Li, Y.; Tan, Y.; Yang, G.F. Bioorg. Med. Chem. 2007, 15, 5191-5198.
[3] (a) Fliur, M.; Ghenadie, R.; Serghei, P.; Robert, R. Bioorg. Med. Chem. 2005, 13, 4842-4845. (b) Alagawadi, K.R.; Mahajanshetti, C.S.; Jalalpure, S.S. Indian J. Heterocyclic Chem. 2005, 14, 315-318.
[4] (a) Chen, C.J.; Song, B.A.; Yang, S.; Xu, G.F.; Bhadury, P.S.; Jin, L.H.; Hu, D.Y.; Li, Q.Z.; Liu, F.; Xue, W.; Lu, P.; Chen, Z. Bioorg. Med. Chem. 2007, 15, 3981-3989. (b) Chen, H.; Li, Z.; Han, Y. J. Agric. Food Chem. 2000, 48, 5312-5315. (c) Huang, W.; Zhao, P.L.; Liu, C.L.; Chen, Q.; Liu, Z.M.; Yang, G.F. J. Agric. Food Chem. 2007, 55, 3004-3010. (d) Li, Y.; Liu, J.; Zhang, H.Q.; Liu, Z.J. Bioorg. Med. Chem. Lett. 2006, 16, 2278-2282.
[5] (a) Zarghi, A.; Tabatabai, T.; Faizi, M.; Ahadian, A.; Navabi, P.; Zanganehb, V.; Shafieec, A. Bioorg. Med. Chem. Lett. 2005, 15, 1863-1865. (b) Almasirad, A.; Tabatabai, S.A.; Faizi, M.; Kebriaeezadeh, A.; Mehrabi, N.; Dalvandi, A.; Shafiee, A. Bioorg. Med. Chem. 2004, 14, 6057-6059.
[6] (a) Partyka, R.A.; Crenshaw, R.R. U.S. Pat. 4001238, 1977. (b) Akbarzadeh, T.; Tabatabai, S.A.; Khoshnoud, M.J.; Shafaghi, B.; Shafiee, A. Bioorg. Med. Chem. 2003, 11, 769-773.
[7] (a) Abbas, S.E.; Abou-Youssef, H.E.; El-Taliawi, G.M.; Hassan, A.B. Egypt. J. Pharm. Sci. 1991, 32, 515-527. (b) Dodd, D.S.; Nishi, T. U.S. Pat. 5670526, 1979. (c) Du, W.; Hardouin, C.; Cheng, H.; Hwang, I.; Boger, D. L. Bioorg. Med. Chem. Lett. 2005, 15, 103-106.
[8] (a) Gregory, I.; James, R.; Fuchs, B.; Ishikawa, H.; Tao, H.; Yuan, Z.; Boger, D. J. Am. Chem. Soc. 2006, 128, 10589-10595. (b) Liu, Z.; Zhao, J.; Huang X. Bioorg. Med. Chem. Lett. 2006, 16, 1828-1830.
[9] (a) Sun, Q.; Wang, Y.Q.; Ge, Z.M.; Cheng, T.M.; Li, R.T. Synthesis. 2004, 7, 1047-1051. (b) Zhao, Y.; Ge, Z.M.; Cheng, T.M.; Li, R.T. Synlett. 2007, 10, 1529-1532. (c) Lei, M.; Shi, L.X.; Li, G.; Chen, S.L.; Fang, W.H.; Ge, Z.M.; Cheng, T.M.; Li, R.T. Tetrahedron. 2007, 63, 7892-7898.
[10] Zarghi, A.; Tabatabai, T.; Faizi, M.; Ahadian, A.; Navabi, P.; Zanganehb, V.; Shafieec, A. Bioorg. Med. Chem. Lett. 2005, 15, 1863-1865.
[11] (a) Ram, V.J. J. Heterocycl. Chem. 1988, 25, 253-256. (b) Okad, Y. Jpn. Tokkyo Koho. J.P. Pat. 45024982, 1970. (c) Giri, S.; Singh, H.; Yadav, L.D. Agric. Biol. Chem. 1976, 40, 17-21. (d) El-Shafei, A.K.; Ghattas, A.; Gad, F. Revue Roumaine de Chimie. 1985, 30, 817-822. (e) Alam, L.M.; Koldobskii, G.I. Tetrazoles. Russ. J. Org. Chem. 1997, 33, 1149-1155. (f) Ioannisyan, E.M.; Chernitsa, B.V.; Yakovlev, V.V. Russ. J. Org. Chem. 2006, 42, 1089-1090. (g) Mir, I.; Siddiqui, M.T.; Comrie, A.M. J. Chem. Soc. 1971, 16, 2798-2799.