Review About the Synthesis of 1,3-Benzothiazinone Derivatives

doi:10.6023/cjoc201603034

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2024-2038.DOI: 10.6023/cjoc201603034 Previous Articles Next Articles

REVIEW

1,3-苯并噻嗪酮类衍生物合成方法的研究进展

李闪闪, 洪海龙, 竺宁, 韩利民, 吕佳媛

内蒙古工业大学化工学院呼和浩特 010051

收稿日期:2016-03-20 修回日期:2016-05-06 发布日期:2016-05-19
通讯作者: 洪海龙, 竺宁 E-mail:honghailong_1979@163.com;zhuning2622@yahoo.com
基金资助:
国家自然科学基金（Nos.21362019，21666026）、内蒙古自然科学基金（No.2016MS0207）、内蒙古自治区教育厅研究生科研创新基金（No.S20151012805）资助项目.

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

Li Shanshan, Hong Hailong, Zhu Ning, Han Limin, Lü Jiayuan

Chemical Engineering College, Inner Mongolia University of Technology, Hohhot 010051

Received:2016-03-20 Revised:2016-05-06 Published:2016-05-19
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21362019, 21666026), the Natural Science Foundation of Inner Mongolia (No.2016MS0207) and the Graduate Student Scientific Research Innovation Foundation of the Department of Education of Inner Mongolia Autonomous Region (No.S20151012805).

1,3-Benzothiazinone derivatives have widely bioactivities. So the methods for the synthesis of these 1,3-benzothiazinone derivatives have attracted enormous attentions worldwide. From the method of introducing sulfur atom and the reaction mechanism for the formation of benzothiazinone derivatives, the method of synthesizing 1,3-benzothiazinone derivatives has been summarized in this review. So the thiophenol derivatives, disulfide derivatives, the same carbon connected with amino and mercapto derivatives, isothiocyanate derivatives and some smaller sulfur molecules are used as starting materials.

Key words: 1,3-benzothiazinone, sulfur source, synthetic methods, reaction mechanism

Cite this article

Li Shanshan, Hong Hailong, Zhu Ning, Han Limin, Lü Jiayuan. Review About the Synthesis of 1,3-Benzothiazinone Derivatives[J]. Chin. J. Org. Chem., 2016, 36(9): 2024-2038.

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[1] Ajani, O. O. Arch. Pharm. Chem. Life Sci. 2012, 345, 841.
[2] (a) Suazo, P. A.; Tognarelli, E. I.; Kalergis, A. M.; Gonzalez, P. A. Med. Microbiol. Immunol. 2015, 204, 161. (b) Chamoun, A. M.; Chockalingam, K.; Bobardt, M.; Simeon, R.; Chang, J.; Gallay, P.; Chen, Z. Antimicrob. Agents Chemother. 2012, 56, 672. (c) Mizuhara, T.; Oishi, S.; Ohno, H.; Shimura, K.; Matsuoka, M.; Fujii, N. Bioorg. Med. Chem. 2012, 20, 6434.
[3] Saunthwal, R. K.; Patel, M.; Kumar, S.; Verma, A. K. Tet-rahedron Lett. 2015, 56, 677.
[4] Hong, X. C. Ph.D. Dissertation, University of Mis-souri-Columbia, Missouri, 2005.
[5] You, Q. D. Medicine Chemistry, The Medicine Science and Technology Press of China, Beijing, 2011, p. 41, p. 477, p. 488(in Chinese). (尤启东, 药物化学, 中国医药科技出版社, 北京, 2011, p. 41, p. 477, p. 488.)
[6] Lu, H. P.; Edwards, M.; Wang, Q. Z.; Zhao, H. J.; Fu, H. W.; Huang, J. Z.; Gatehouse, A.; Shu, Q. Y. J. Zhejiang Univ. Sci. B 2015, 16, 113.
[7] Yongpruksa, N. Ph.D. Dissertation, University of Mis-souri-Columbia, Missouri, 2011.
[8] Ingr, J. S.; Mcclella, E. W. J. Chem. Soc. 1947, 763.
[9] Liu, C. M.; Li, B.; Shen, Y. H.; Zhang, W. D. J. Nat. Prod. 2010, 73, 1582.
[10] Khanmiri, R. H.; Moghimi, A.; Shaabani, A.; Valizadeh, H.; Ng, S. Mol. Diversity 2014, 18, 769.
[11] Popio?ek, ?. Am. Chem. Sci. J. 2015, 6, 231.
[12] (a) Popio?ek, ?.; Biernasiuk, A.; Malm, A. J. Heterocycl. Chem. 2016, 53, 479. (b) Gen, H. J.; Gao, N.; Li, Y. X.; Zhang, W. J.; Su, X.; Guo, C. J. Shenyang Pharm. Univ. 2012, 29, 834(in Chinese). (耿红健, 高宁, 李裕鑫, 张卫军, 苏昕, 郭春, 沈阳药科大学学报, 2012, 29, 834.)
[13] (a) Wang, S.; Fang, K.; Dong, G.; Chen, S.; Liu, N.; Miao, Z.; Yao, J.; Li, J.; Zhang, W.; Sheng, C. J. Med. Chem. 2015, 58, 6678. (b) Kamel, M. M.; Ali, H. I.; Anwar, M. M.; Mohamed, N. A.; Soliman, A. M. Eur. J. Med. Chem. 2010, 45, 572. (c) Chen, D. B.; Wu, J. S.; Yang, J. G.; Huang, L.; Xiang, Y. B.; Bao, W. L. Tetrahedron Lett. 2012, 53, 7104.
[14] Solomon, V. R.; Haq, W.; Srivastava, K.; Puri, S. K.; Katti, S. J. Med. Chem. 2007, 50, 394.
[15] (a) Yu, L.; Wei, Y. WO 2013185507, 2013[Chem. Abstr. 2013, 60, 86543]. (b) Makarov, V.; Cole, S. T.; Möllmann, U. EP 2029583, 2007[Chem. Abstr, 2007, 147, 541887].
[16] (a) Makarov, V.; Lechartier, B.; Zhang, M.; Neres, J.; Sar, A. M.; Raadsen, S. A.; Hartkoorn, R. C.; Ryabova, O. B.; Vocat, A.; Decosterd, L.A.; Widmer, N.; Buclin, T.; Bitter, W.; Andries, K.; Pojer, F.; Dyson, P. J.; Cole, S. T. EMBO Mol. Med. 2014, 6, 372. (b) Lechartier, B.; Hartkoorn, R. C.; Cole, S. T. Antimicrob. Agents Chemother. 2012, 56, 5790. (c) Tiwari, R.; Miller, P. A.; Chiarelli, L. R.; Mori, G.; Šarkan, M.; Centárová, I.; Cho, S.; Mikušová, K.; Franzblau, S. G.; Oliver, A. G.; Miller, M. J. ACS Med. Chem. Lett. 2016, 7, 266. (d) Tiwari, R.; Miller, P. A.; Cho, S.; Franzblau, S. G.; Miller, M. J. ACS Med. Chem. Lett. 2015, 6, 128. (e) Tiwari, R.; Möllmann, U.; Cho, S.; Franzblau, S. G.; Miller, P. A.; Miller, M. J. ACS Med. Chem. Lett. 2014, 5, 587.
[17] Zarghi, A.; Zebardast, T.; Daraie, B.; Hedayati, M. Bioorg. Med. Chem. 2009, 17, 5369.
[18] Gaudilliere, B.; Jacobelli, H. WO 2004000321, 2003[Chem. Abstr. 2003, 140, 59649].
[19] Fukui, K. US 20060019207, 2006[Chem. Abstr. 2006, 144, 180847].
[20] Szabó, J. Chem. Heterocycl. Commun. 1979, 239.
[21] Fodor, L.; Gábor, B.; Jari, S.; Pihlaja, K. J. Heterocycl. Chem. 2002, 39, 927.
[22] Szabó, J.; Szucs., E.; Fodor, L.; Katócs, Á.; Bernath, G. Tetrahedron 1988, 44, 2985.
[23] Benedini, F.; Bertolini, G.; Ferrario, F.; Guindani, R.; Sala, A. J. Heterocycl. Chem. 1994, 31, 1589.
[24] Verma, S. K.; Ghorpade, R.; Pratap, A.; Kaushik, M. P. Tetrahedron Lett. 2012, 53, 2373.
[25] Zhu, X. X.; Yu, Q. S.; Greig, N. H.; Flippen-Anderson, J. L.; Brossi, A. Heterocycles 2003, 59, 115.
[26] Schiff, H. Liebigs Ann. Chem. 1864, 131, 118.
[27] (a) Qin, W.; Long, S.; Panunzio, M.; Biondi, S. Molecules 2013, 18, 12264. (b) Surrey, A. R. J. Am. Chem. Soc. 1947, 69, 2911.
[28] Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
[29] Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
[30] Nelson, D. A. J. Org. Chem. 1972, 37, 1447.
[31] (a) Kitsiou, C.; Unsworth, W. P.; Coulthard, G.; Taylor, R. J. K. Tetrahedron 2014, 70, 7172. (b) Unsworth, W. P.; Kitsiou, C.; Taylor, R. J. K. Org. Lett. 2013, 15, 258.
[32] Johannes, K.; Martens, J. Tetrahedron 2010, 66, 242.
[33] Tierney, J. J. Heterocycl. Chem. 1989, 26, 997.
[34] Silverberg, L. J.; Pacheco, C. N.; Lagalante, A.; Cannon, K. C.; Bachert, J. T.; Xie, Y.; Baker, L.; Bayliff, J. A. Int. J. Chem. 2015, 7, 150.
[35] Mallakpour, S.; Yousefian, H. J. Braz. Chem. Soc. 2007, 18, 1220.
[36] Pritchard, K. M.; Al-Rawi, J. M.; Hughes, A. B. Synth. Commun. 2005, 35, 1601.
[37] Shestakov, A. S.; Prezent, M. A.; Zlatoustovskaya, E. O.; Shikhaliev, K. S.; Falaleev, A. V.; Sidorenko, O. E. Chem. Heterocycl. Compd. 2015, 51,370.
[38] Elghandour, A. H. H.; Ramiz, M. M. M.; Ibrahim, M. K. A.; Elmoghayar, M. R. H. Org. Prep. Proced. Int. 1989, 21, 479.
[39] Ibrahim, N. S.; Abed, N. M.; Kandeel, Z. E. Heterocycles 1984, 22,1677.
[40] Allam, Y. A.; Chabaka, L. M.; Nawwar, G. A. M. Heteroat. Chem. 2000, 11, 209.
[41] Zhu, N.; Zhang, Z. W.; Gao, M.; Han, L. M.; Suo, Q. L.; Hong, H. L. Chin. J. Org. Chem. 2013, 33, 1423(in Chinese). (竺宁, 张志伟, 高敏, 韩利民, 索全伶, 洪海龙, 有机化学, 2013, 33, 1423.)
[42] Golec, Jr. F.A.; Paul, L.; Lloyd, J. R. J. Heterocycl. Chem. 1983, 20, 1755.
[43] (a) Zhu, N.; Du, G. Y.; Han, L. M.; Hong, H. L.; Suo, Q. L. Heterocycles 2015, 91, 1723. (b) Liu, B.; Zhu, N.; Hong, H. L.; Han, L. M. Tetrahedron 2015, 71, 9287.
[44] Bakthadoss, M.; Selvakumar, R.; Srinivasan, J. Tetrahedron Lett. 2014, 55, 5808.
[45] Nageswar, Y. V. D.; Murty, M. S. R.; Ramalingam, T.; Sattur, P. B. Indian J. Chem. 1988, 27B, 1142.
[46] Han, S.; Yoon, Y. Y.; Jung, O. S.; Lee, Y. A. Chem. Commun. 2011, 47, 10689.
[47] Dolbier Jr, W. R.; Burkholder, C.; Abboud, K. A.; Loehle, D. J. Org. Chem. 1994, 59, 7688.
[48] Lipunova, G. N.; Nosova, E. V.; Mokrushina, G. A.; Ogloblina, E. G.; Aleksandrov, G. G.; Charushin, V. N. Russ. J. Org. Chem. 2003, 39, 248.
[49] Nosova, E. V.; Liponova, G. N.; Kravchenko, M. A.; Laeva, A. A.; Charushin, V. N. Pharm. Chem. J. 2008, 42, 169.
[50] Huang, L.; Yang, J.; Xu, L.; Wu, X.; Yu, L.; Bao, W.; Chen, D. Heteroat. Chem. 2015, 26, 361.
[51] Takagi, K. Chem. Lett. 1990, 2205.
[52] Sainsbury, M. Oxazines. Thiazines and Their Benzo Derivatives, 1984, p. 995.
[53] (a) Nosova, E. V.; Lipunova, G. N.; Laeva, A. A.; Charushin, V. N. Russ. J. Org. Chem. 2006, 42, 1544. (b) Nosova, E. V.; Lipunova, G. N.; Laeva, A. A.; Sidorova, L. P.; Charushin, V. N. Russ. J. Org. Chem. 2007, 43, 68.
[54] (a) Gao, C.; Ye, T. H.; Wang, N. Y.; Zeng, X. X.; Zhang, L. D.; Xiong, Y.; You, X. Y.; Xia, Y.; Xu, Y.; Peng, C. T.; Zuo, W. Q.; Wei, Y.; Yu, L. T. Bioorg. Med. Chem. Lett. 2013, 23, 4919. (b) Peng, C. T.; Gao, C.; Wang, N. Y.; You, X. Y.; Zhang, L. D.; Zhu, Y. X.; Xv, Y.; Zuo, W. Q.; Ran, K.; Deng, H. X.; Lei, Q.; Xiao, K. J.; Yu, L. T. Bioorg. Med. Chem. Lett. 2015, 25, 1373.
[55] Nosova, E. V.; Lipunova, G. N.; Laeva, A. A.; Charushin, V. N. Russ. Chem. Bull. 2005, 54, 733.
[56] Nosova, E. V.; Laeva, A. A.; Trashakhova, T. V.; Golovchenko, A. V.; Lipunova, G. N.; Slepukhin, P. A.; Charushin, V. N. Russ. J. Org. Chem. 2009, 45, 904.
[57] Lipunova, G. N.; Nosova, E. V.; Laeva, A. A.; Trashakhova, T. V.; Slepukhin, P. A.; Charushin, V. N. Russ. J. Org. Chem. 2008, 44, 741.
[58] Wright, S. W. J. Heterocycl. Chem. 2001, 38, 732.
[59] Villemagne, B.; Crauste, C.; Flipo, M.; Baulard, A. R.; Deprez, B.; Willand, N. Eur. J. Med. Chem. 2012, 51, 1.
[60] Stalling, T.; Pauly, J.; Kröger, D.; Martens, J. Tetrahedron 2015, 71, 8290.
[61] Kroger, D.; Schluter, T.; Fischer, M.; Geibel, I.; Martens, J. ACS Comb. Sci. 2015, 17, 202.
[62] Rescourio, G.; Howard, A. J. Org. Chem. 2008, 73, 1612.
[63] Wentrup, C.; Bender, H.; Gross, G. J. Org. Chem. 1987, 52, 3838.

1,3-苯并噻嗪酮类衍生物合成方法的研究进展

Review About the Synthesis of 1,3-Benzothiazinone Derivatives

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