SIOC English
有机化学
高级检索

有机化学 >

2014 , Vol. 34 >Issue 3: 485 - 494

DOI: https://doi.org/10.6023/cjoc201310035

综述与进展

三芳基甲烷类化合物合成方法的研究进展

  • 李中贤 ,
  • 王俊伟 ,
  • 赵俊宏 ,
  • 赵灿方 ,
  • 刘小培 ,
  • 余学军
展开
  • a 河南省科学院高新技术研究中心 郑州 450002;
    b 河南省科学院化学研究所 郑州 450002;
    c 郑州铁路疾病预防控制所 郑州 450015

收稿日期: 2013-10-22

  修回日期: 2014-12-03

  网络出版日期: 2013-12-06

基金资助

中国博士后基金（No. 2013M541979）资助项目.

收起

Advanced in the Synthesis of Triarylmethanes

  • Li Zhongxian ,
  • Wang Junwei ,
  • Zhao Junhong ,
  • Zhao Canfang ,
  • Liu Xiaopei ,
  • Yu Xuejun
Expand
  • a High & New Technology Research Center, Henan Academy of Sciences, Zhengzhou 450002;
    b Institute of Chemistry, Henan Academy of Sciences, Zhengzhou 450002;
    c Zhengzhou Railway Center for Disease Control and Prevention, Zhengzhou 450015

Received date: 2013-10-22

  Revised date: 2014-12-03

  Online published: 2013-12-06

Supported by

Project supported by the China Postdoctoral Science Foundation (No. 2013M541979).

Fold

摘要

三芳基甲烷类化合物在材料、药物、染料、基团保护等领域有着重要的用途，三芳基甲烷类化合物的合成方法是近年来有机化学中研究的热点之一. 结合作者和国内外学者对这方面的相关研究，综述了三芳基甲烷类化合物的合成方法研究，并对三芳基甲烷类化合物合成方法的发展进行探讨.

关键词： 三芳基甲烷; 傅克反应; 偶联反应; 缩合反应

本文引用格式

李中贤 , 王俊伟 , 赵俊宏 , 赵灿方 , 刘小培 , 余学军 . 三芳基甲烷类化合物合成方法的研究进展[J]. 有机化学, 2014 , 34(3) : 485 -494 . DOI: 10.6023/cjoc201310035

Abstract

Triarylmethanes (TRAMs) constitute an important class of compounds that are ubiquitous in material, medicals, and dyes. Numerous methods have been developed for the synthesis of TRAMs. This minireview critically presents the synthesis of TRAMs to encourage further research activities in this promising area of the TRAMs.

Key words： triarylmethane; Friedel-Crafts reaction; coupling reactions; condensation reaction

参考文献

[1] Irie, M. J. Am. Chem. Soc. 1983, 105, 2078.



[2] Muthyala, R.; Katritzky, A. R.; Lan, X. Dyes Pigm. 1994, 25, 303.



[3] Hirohiko, H.; Shunpei, T.; Issei, O.; Kazunari, M.; Hidetake, S.; Isao, Y.; Yasushi, M.; Koji, A. Chem. Eur. J. 2011, 17, 1122.



[4] Kocieński, P. J. Protecting Groups, 3rd ed., Georg Thieme, Stuttgart, 2003.



[5] (a) Sanguinet, L.; Twieg, R. J.; Wiggers, G.; Mao, G.; Singer, K. D.; Petschek, R. G. Tetrahedron Lett. 2005, 46, 5121.



(b) Shagufta, S. K. D.; Panda, G. Tetrahedron Lett. 2005, 46, 3097.



[6] (a) Poupelin, J. P.; Saint-Ruf, G.; Foussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lacroix, R. Eur. J. Med. Chem. 1978, 13, 67.



(b) Yamato, M.; Hashigaki, K.; Yasumoto, Y.; Sakai, J.; Luduena, R. E.; Banerjee, A.; Tsukagoshi, S.; Tashiro, T.; Tsuruo, T. J. Med. Chem. 1987, 30, 1897.



(c) Sato, T.; Kise, H. Yukagaku 1988, 37, 166.



(d) Asakura, K.; Matsumura, S.; Yoshikawa, S. Yukagaku 1988, 37, 265.



(e) Patel, V. F.; Hardin, J. N.; Starling, J. J.; Mastro, J. M. Bioorg. Med. Chem. Lett. 1995, 5, 507.



(f) Mibu, N.; Sumoto, K. Chem. Pharm. Bull. 2000, 48, 1810.



(g) McNaughton-Smith, G. A.; Rigdon G. C.; Stocker, J. WO 2000050026, 2000[Chem. Abstr. 2000, 133, 187954].



(h) Santhosh, K. C.; Paul, G. C.; De Clercq, E.; Pannecouque, C.; Witvrouw, M.; Loftus, T. L.; Turpin, J. A.; Buckheit, R. W., Jr.; Cushman, M. J. Med. Chem. 2001, 44, 703.



(i) Sumoto, K.; Mibu, N.; Yokomizo, K.; Uyeda, M. Chem. Pharm. Bull. 2002, 50, 298.



(j) Finer, J. T.; Chabala, J. C.; Lewis, E. WO 2002056880, 2002, [Chem. Abstr. 2002, 137, 124985].



(k) Mibu, N.; Yokomizo, K.; Uyeda, M.; Sumoto, K. Chem. Pharm. Bull. 2003, 51, 1325;



[7] Rueping, M.; Nachtsheim, B. J.; Ieawsuwan, W. Adv. Synth. Catal. 2006, 348, 1033.



[8] Lin, S.; Lu, X. J. Org. Chem. 2007, 72, 9757.



[9] Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2006, 348, 691.



[10] Wang, F.; Ueda, W. Chem. Commun. 2008, 3196.



[11] Mertins, K.; Iovel, I.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 238.



[12] Iovel, I.; Mertins, K.; Kischel, J.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 3913.



[13] Srihari, P.; Bhunia, D. C.; Sreedhar, P.; Yadav, J. S. Synlett 2008, 1045.



[14] Shirakawa, S.; Kobayashi, S. Org. Lett. 2007, 9, 311.



[15] Werbel, L. M.; Elslager, E. F.; Pearlman, W. M. J. Org. Chem. 1964, 29, 967.



[16] Katritzky, A. R.; Gupta, V.; Garot, C.; Stevens, C. V.; Gordeev, M. F. Heterocycles 1994, 38, 345;



[17] Katritzky, A. R.; Xie, L.; Fan, W. Q. J. Org. Chem. 1993, 58, 4376.



[18] Das, S. K.; Shaguftu; Panda, G. Tetrahedron Lett. 2005, 46, 3097.



[19] Ballester, M.; Riera, J.; Castaner, J.; Rovira, C.; Annet, O. Synthesis, 1986, 64.



[20] Katritzky, A. R.; Toader, D. J. Org. Chem. 1997, 62, 4137.



[21] Wang, B.-Q.; Xiang, S.-K.; Sun, Z-P.; Guan, B.-T.; Hu, P.; Zhao, K.-Q.; Shi, Z.-J. Tetrahedron Lett. 2008, 49, 4310.



[22] Esquivias, J.; Arrayas, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 629.



[23] Liu, C.-R.; Li, M.-B.; Yang, C.-F.; Tian, S.-K. Chem. Commun. 2008, 1249.



[24] Wang, Z.-Y.; Sun, X.-Y.; Wu, J. Tetrahedron 2008, 64, 5013.



[25] (a) Thirupathi, P.; Kim, S. S. Eur. J. Org. Chem. 2010, 1798.



(b) Thirupathi, P.; Kim, S. S. J. Org. Chem. 2010, 75, 5240.



[26] (a) He, Q.-L.; Sun, F.-L.; Zheng, X.-J.; You, S.-L. Synlett 2009, 1111.



(b) Sun, F.-L.; Zheng, X.-J.; Gu, Q.; He, Q.-L.;You, S.-L. Eur. J. Org. Chem. 2010, 47.



[27] Paresh, N. C.; Arnab, K. M.; Swapna, S. M.; Sujit, R. Tetrahedron 2013, 69, 2816.



[28] Khosropour, A. R.; Esmaeilpoor, K.; Moradie, A. J. Iran. Chem. Soc. 2006, 3, 81.



[29] Paul, A. M.; Khandekar, A. C.; Khadilkar, B. M. J. Chem. Res., Synop. 2003, 168.



[30] Ohishi, T.; Kojima, T.; Matsuoka, T.; Shiro, M.; Kotsuki, H. Tetrahedron Lett. 2001, 42, 2493.



[31] Abaev, V. T.; Tsiunchik, F. A.; Gutnov, A. V.; Butin, A. V. Tetrahedron Lett. 2006, 47, 4029.



[32] Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 7, 5857.



[33] Nair, V.; Vidya, N.; Abhilash, K. G. Synthesis 2006, 3647.



[34] Podder, S.; Choudhury, J.; Roy, U. K.; Roy, S. J. Org. Chem. 2007, 72, 3100.



[35] Mibu, N.; Sumoto, K. Chem. Pharm. Bull. 2000, 48, 1810.



[36] (a) Li, Z.; Duan, Z.; Kang, J.; Wang, H.; Yu, L.; Wu, Y. Tetrahedron 2008, 64, 1924.



(b) Li, Z.; Duan, Z.; Wu, Y. Chin. Chem. Lett. 2009, 20, 511.



(c) Li, Z.; Zhao, C.; Liu, X.; Xu, D.; Yu, X. Henan Sci. 2011, 29(2), 145 (in Chinese).



(李中贤, 赵灿方, 刘小培, 徐丹, 余学军, 河南科学, 2011, 29(2), 145.)



[37] Kodomari, M.; Nagamatsu, M.; Akaike, M.; Aoyama, T. Tetrahedron Lett. 2008, 49, 2537.



[38] Prakash, G. K. S.; Panja, C.; Shakhmin, A.; Shah, E.; Mathew, T.; Olah, G. A. J. Org. Chem. 2009, 74, 8659.



[39] Li, H.; Yang, J.; Liu, Y.; Li, Y. J. Org. Chem. 2009, 74, 6797.



[40] Jaratjaroonphong, J.; Sathalalai, S.; Techasauvapak, P.; Reutrakul, V. Tetrahedron Lett. 2009, 50, 6012.



[41] Chandrasekhar, S.; Khatun, S.; Rajesh, G.; Raji Reddy, C. Tetrahedron Lett. 2009, 50, 6693.



[42] Leng, Y.; Chen, F.; Zuo, L.; Duan, W. Tetrahedron Lett. 2010, 51, 2370.



[43] Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mohammadiannejad-Abbasabadi, K.; Khavasi, H. R. Eur. J. Org. Chem. 2011, 1357.



[44] Barbero, M.; Cadamuro, S.; Dughera, S.; Magistris, C.; Venturello, P. Org. Biomol. Chem. 2011, 9, 8393.



[45] Thirupathi, P.; Neupane, L. N.; Lee, K. H. Tetrahedron 2011, 67, 7301.



[46] Wilsdorf, M.; Leichnitz, D.; Reissig, H.-U. Org. Lett. 2013, 15, 2494.



[47] Muthyala, R.; Katrizky, A. R.; Lan, X. Dyes Pigm. 1994, 25, 303.



[48] Niwa, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 2373.



[49] Yu, J.-Y.; Kuwano, R. Org. Lett. 2008, 10, 973.



[50] (a) Bellomo, A.; Zhang, J.; Trongsiriwat, N.; Walsh, P. J. Chem. Sci. 2013, 4, 849.



(b) Zhang, J.; Bellomo, A.; Creamer, A. D.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2012, 134, 13765.



[51] Taylor, B. L. H.; Harris, M. R.; Jarvo, E. R. Angew. Chem., Int. Ed. 2012, 51, 7790.



[52] Harris, M. R.; Hanna, L. E.; Greene, M. A.; Moore, C. E.; Jarvo, E. R. J. Am. Chem. Soc. 2013, 135, 3303.



[53] Zhou, Q.; Srinivas, H. D.; Dasgupta, S.; Watson, M. P. J. Am. Chem. Soc. 2013, 135, 3307.



[54] Xia, Y.; Hu, F.; Liu, Z.; Qu, P.; Ge, R.; Ma, C.; Zhang, Y.; Wang, J. Org. Lett. 2013, 15, 1784.



[55] Gordon, P. E.; Fry, A. J. Tetrahedron Lett. 2001, 42, 831.



[56] Cannella, R.; Clerici, A.; Pastori, N.; Regolini, E.; Porta, O. Org. Lett. 2005, 7, 645.



[57] (a) Ahmad, R.; Riahi, A.; Langer, P. Tetrahedron Lett. 2009, 50, 1490.



(b) Ahmad Khera, R.; Ullah, I.; Ahmad, R.; Riahi, A.; Hung, N. T.; Sher, M.; Villinger, A.; Fischer, C.; Langer, P. Tetrahedron 2010, 66, 1643.



[58] Gonzalez, J.; Gonzalez, J.; Perez-Calleja, C.; Lopez, L. A.; Vicente, R. Angew. Chem., Int. Ed. 2013, 52, 5853.

Options
文章导航

/

〈 〉