芳香杂环硫醚类化合物的合成研究
收稿日期: 2016-02-22
修回日期: 2016-03-25
网络出版日期: 2016-04-15
基金资助
山西省科技创新(No. 2014101011)资助项目.
Synthesis of Aromatic Heterocyclic Sulfide Compounds
Received date: 2016-02-22
Revised date: 2016-03-25
Online published: 2016-04-15
Supported by
Project supported by the Science and Technology Innovation Project of Shanxi Province (No. 2014101011).
张变香 , 亢永强 , 史瑞雪 . 芳香杂环硫醚类化合物的合成研究[J]. 有机化学, 2016 , 36(8) : 1814 -1823 . DOI: 10.6023/cjoc201602021
Recently, the aromatic heterocyclic sulfide was widely used in medical and functional materials as an intermediate in organic chemistry and a structural unit in drug synthesis. Their synthetic method has become one of the hot research areas. This review summarizes the recent synthetic methods of aromatic heterocyclic thioether, which mainly involves metallic catalyzed and no metal-catalyzed methods, as well as benzene alkyne intermediate method. Some of their synthetic mechanisms were illustrated.
[1] (a) Chen, H.-Y.; Peng, W.-T.; Lee, Y.-H.; Chang, Y.-L.; Chen, Y.-J.; Lai, Y.-C.; Jheng, N.-Y.; Chen, H.-Y. Organometallics 2013, 32, 5514.
(b) Gao, S.; Zeng, Q. L.; Tang, Y. H.; Liu, Y.; Dong, J. Y.; Zhang, B. S. Prog. Chem. 2010, 1760 (in Chinese).
(高珊, 曾庆乐, 唐红艳, 刘洋, 董俊宇, 张斌彬, 化学进展, 2010, 1760.)
(c) Zha, C. J. M.S. Thesis, Hunan University, Changsha, 2011 (in Chinese).
(查长军, 硕士论文, 湖南大学, 长沙, 2011.)
(d) Argüello, J. E.; Schmidt, L. C.; Peñéñory, A. B. Org. Lett. 2003, 5, 4133.
(e) Yao, H.; Richardson, D. E. J. Am. Chem. Soc. 2003, 125, 6211.
[2] Zhou, C.; Xu, J. X. Prog. Chem. 2012, 24, 338 (in Chinese)
(周婵, 许家喜, 化学进展, 2012, 24, 338.)
[3] Yu, S. X.; Liu, H. P.; Fu, C. J. Acta Sci. Nat. Univ. Normal Hunan 2000, 23, 41 (in Chinese).
(俞善信, 刘惠平, 傅长金, 湖南师范大学自然科学学报, 2000, 23, 41.)
[4] (a) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
(b) Shi, S. H.; Tu, X. Z.; Zhang, X. P.; Dai, C.; Zeng, Q. L. Guangzhou Chem. Ind. 2012, 40, 1 (in Chinese).
(史少辉, 涂兴钊, 张小平, 代川, 曾庆乐, 广东化工, 2012, 40, 1.)
(c) Tian, F. S.; Wang, Q. Z.; Yang, Z. G.; Fan, X. Y.; Wu, L. J. Zhoukou Normal Univ. 2014, 31, 90 (in Chinese).
(田丰收, 王全忠, 杨志广, 凡晓宇, 武兰, 周口师范学院学报, 2014, 31, 90.)
(d) Zeng, Q. L.; Gao, S.; Allan, K. C. Min-Rev. Org. Chem. 2013, 10, 198.
[5] Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13.
[6] (a) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Chem. Soc. Jpn. 1980, 53, 1385.
(b) Murahashi, S.; Yamamura, M.; Yanagisawa, K.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2408.
(c) Foa, M.; Santi, R.; Garavaglia, F. J. Organomet. Chem. 1981, 206, C29.
[7] Dickens, M. J.; Gilday, J. P.; Mowlem, T. J.; Widdowson, D. A. Tetrahedron 1991, 47, 8621.
[8] Guo, Y. J.; Tang, R. Y.; Li, J. H.; Zhong, P.; Zhang, X. G. Adv. Synth. Catal. 2009, 351, 2615.
[9] (a) Wu, G. L.; Liu, Q.; Shen, Y. L.; Wu, W. T.; Wu, L. M. Tetrahedron Lett. 2005, 46, 5831.
(b) Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. Org. Lett. 2004, 6, 819.
(c) La Regina, G.; Edler, M. C.; Brancale, A.; Kandil, S.; Coluccia, A.; Piscitelli, F.; Hamel, E.; De Martino, G.; Matesanz, R.; Diaz, J. F.; Scovassi, A. I.; Prosperi, E.; Lavecchia, A.; Novellino, E.; Artico, M.; Silvestri, R. J. Med. Chem. 2007, 50, 2865.
(d) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(e) Yadav, J. S.; Reddy, B. V. S.; Reddy, Y. J. Tetrahedron Lett. 2007, 48, 7034.
[10] Chen, Y.; Cho, C. H.; Shi, F.; Larock, R. C. J. Org. Chem. 2009, 74, 6802.
[11] Anbarasan, P.; Neumann, H.; Beller, M. Chem. Commun. 2011, 47, 3233.
[12] (a) Cong, M.; Fan, Y.; Raimundo, J.-M.; Xia, Y.; Liu, Y.; Quelever, G.; Qu, F.-Q.; Peng, L. Chem.-Eur. J. 2013, 19, 17267.
(b) Cong, M.; Fan, Y.; Raimundo, J.-M.; Tang, J.; Peng, L. Org. Lett. 2014, 16, 4074.
[13] Taniguchi, N.; Onami, T. J. Org. Chem. 2004, 69, 915.
[14] (a) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
(b) Taniguchi, N. Synlett. 2006, 1351.
[15] Luo, P.-S.; Yu, M.; Tang, R.-Y.; Zhong, P.; Li, J.-H. Tetrahedron Lett. 2009, 50, 1066.
[16] Fukuzawa, S.-I.; Shimizu, E.; Atsuumi, Y.; Haga, M.; Ogata, K. Tetrahedron Lett. 2009, 50, 2374.
[17] Ranjit, S.; Lee, R.; Heryadi, D.; Shen, C.; Wu, J.; Zhang, P.; Hang, K. W.; Liu, X. J. Org. Chem. 2011, 76, 8999.
[18] Dai, C.; Xu, Z.; Huang, F.; Yu, Z.; Gao, Y.-F. J. Org. Chem. 2012, 77, 4414.
[19] He, Z.; Luo, F.; Li, Y.; Zhu, G. Tetrahedron Lett. 2013, 54, 5907.
[20] Ke, F.; Qu, Y.; Jiang, Z.; Li, Z.; Wu, D.; Zhou, X. Org. Lett. 2011, 13, 454.
[21] Alves, D.; Lara, R. G.; Contreira, M. E.; Radatz, C. S.; Duarte, L. F. B.; Perin, G. Tetrahedron Lett. 2012, 53, 3364.
[22] He, G.; Huang, Y.; Tong, Y.; Zhang, J.; Zhao, D.; Zhou, S.; Han, S. Tetrahedron Lett. 2013, 54, 5318.
[23] (a) Zhang, B. X.; Chen, K.; Yang, L. H.; Xu, Y. T.; Zhang, R. J.; Zhang, L. N.; Shi, R. X. Chin. J. Org. Chem. 2015, 35, 905 (in Chinese).
(张变香, 陈凯, 杨丽花, 许钰涛, 张瑞杰, 张利娜, 史瑞雪, 有机化学, 2015, 35, 905.)
(b) Zhang, B. X.; Guo, Y. L.; Yang, L. H.; Shi, R. X. Imaging Sci. Photochem. 2015, 33, 177 (in Chinese).
(张变香, 郭一力, 杨丽花, 史瑞雪, 影像科学与光化学, 2015, 33, 177.)
[24] Jiang, X. F.; Qiao, Z. J. CN 104725172A, 2015 [Chem. Abstr. 2015, 163, 191616].
[25] Singh, N.; Singh, R.; Raghuvanshi, D. S.; Singh, K. N. Org. Lett. 2013, 15, 5874.
[26] Zhang, B. X.; Yang, L. H.; Shi, R. X.; Kang, Y. Q. Chin. J. Org. Chem. 2016, 36, 352 (in Chinese).
(张变香, 杨丽花, 史瑞雪, 亢永强, 有机化学, 2016, 36, 352.)
[27] Taniguchi, N. J. Org. Chem. 2004, 69, 6904.
[28] Gómez-Benítez, V.; Baldovino-Pantaleón, O.; Herrera-Álvarez, C.; Toscano, R. A.; Morales-Morales, D. Tetrahedron Lett. 2006, 47, 5059.
[29] Gendre, F.; Yang, M.; Diaz, P. Org. Lett. 2005, 7, 2719.
[30] Duan, Z.; Ranjit, S.; Zhang, P.; Liu, X. Chem. Eur. J. 2009, 15, 3666.
[31] Wang, P.-F.; Wang, X.-Q.; Dai, J.-J.; Feng, Y.-S.; Xu, H.-J. Org. Lett. 2014, 16, 4586.
[32] Ge, W.; Wei, Y. Green Chem. 2012, 14, 2066.
[33] Azeredo, J. B.; Godoi, M.; Martins, G. M.; Silveira, C. C.; Braga, A. L. J. Org. Chem. 2014, 79, 4125.
[34] Yang, F. L.; Tian, S. K. Angew. Chem., Int. Ed. 2013, 52, 4929.
[35] Hou, W.; Wei, Q.; Liu, G.; Chen, J.; Guo, J.; Peng, Y. Org. Lett. 2015, 17, 4870.
[36] Kitamura, T.; Zhang, B.-X.; Fujiwara, Y. J. Org. Chem. 2003, 68, 731.
[37] Wang, F.-Y.; Chen, Z.-C.; Zheng, Q.-G. J. Chem. Res. 2004, 127.
[38] Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263.
[39] Zhan, H.; Cao, H.; Qiu, H.; Li, N.; Chen, L.; Liu, J.; Cai, H.; Tan, J. RSC Adv. 2015, 5, 32205.
[40] Li, S. Y. Adv. Fine Petrochem. 2012, 13, 47 (in Chinese).
(李术艳, 精细石油化工进展, 2012, 13, 47.)
[41] Shaw, E.; Bernstein, J.; Losee, K.; Lott, W. A. J. Am. Chem. Soc. 1950, 72, 4362.
[42] Singh, R.; Raghuvanshi, D. S.; Singh, K. N. Org. Lett. 2013, 15, 4202.
[43] Zhang, B. X.; Wu, Q.; Chao, J. B.; Guo, Y. L. Chin. J. Synth. Chem. 2013, 21, 86 (in Chinese).
(张变香, 吴群, 钞建宾, 郭一力, 合成化学, 2013, 21, 86.)
[44] Varun, B. V.; Prabhu, K. R. J. Org. Chem. 2014, 79, 9655.
[45] Gao, Z. C. Chem. Reag. 2013, 35, 1051 (in Chinese).
(高兆昶, 化学试剂, 2013, 35, 1051.)
[46] Yonova, I. M.; Osborne, C. A.; Morrissette, N. S.; Jarvo, E. R. J. Org. Chem. 2014, 79, 1947.
[47] Li, Z. J.; Sun, L.X.; Yang, L.; Zeng, Q. L. Fresen. Environ. Bull. 2015, 24, 3686.
[48] Bhunia, A.; Roy, T.; Pachfule, P.; Rajamohanan, P. R.; Biju, A. T. Angew. Chem., Int. Ed. 2013, 52, 10040.
[49] Lin, W.; Sapountzis, I.; Knochel, P. Angew. Chem. 2005, 44, 4258.
[50] Zhao, J.; Larock, R. C. J. Org. Chem. 2007, 72, 583.
[51] Toledo, F. T.; Marques, H.; Comasseto, J. V.; Raminelli, C. Tetrahedron Lett. 2007, 48, 8125.
[52] Edwards, A. J.; Willis, A. C.; Wenger, E. Organometallics 2002, 21, 1654.
[53] Dong, Y.; Liu, B.; Chen, P.; Liu, Q.; Wang, M. Angew. Chem., Int. Ed. 2014, 53, 3442.
[54] Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 1716.
/
〈 |
|
〉 |