Reviews

Novel Progresses in Synthesis Strategies of Aromatic Azo Derivatives

  • Qin Chuanguang ,
  • Li Yang ,
  • Li Hailiang ,
  • Li Dawei ,
  • Niu Weining ,
  • Shang Xiaoya ,
  • Xu Chunlan
Expand
  • a Key Laboratory of Space Applied Physics and Chemistry of Ministry of Education and Key Laboratory of Macromolecular Science & Technology of Shaanxi Province, Department of Applied Chemistry, School of Natural & Applied Sciences, Northwestern Polytechnical University, Xi'an 710129;
    b School of Life Science, Northwestern Polytechnical University, Xi'an 710072

Received date: 2012-09-28

  Revised date: 2012-11-15

  Online published: 2012-11-20

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 31001012, 31101304, 20802057, 20672086), the Natural Science Basic Research Plan in Shaanxi Province of China (No. 2012JZ2002) and the Postgraduate Pioneer Seed Funding of Northwestern Polytechnical University (No. Z2012198).

Abstract

Aromatic azo derivatives possess a particular character that is the light driven reversible isomerization between their cis- and trans-forms, which makes them excellent candidates to modulate the relative movement of different moieties. They are widely used not only in the traditional chemical industry, but also in many newly rising areas of science, such as photochemical molecular switch, super-molecular chemistry of host-guest recognition, self-assembly liquid crystal material, analysis of biomedical imaging and chemical, light driven molecular motor, and so on. The development of chromophores with characteristics, like high chemical stability, thermal stability over a wide temperature range and having two forms easily detectable by a method that does not cause irreversible molecular alterations, is a major challenge for researchers who focus their interest in this area. With the increasing need for investigating unknown aromatic azo derivatives, many novel efficient synthesis strategies are recently innovated and developed in succession. This critical review covers the various synthetic methods of aromatic azo derivatives reported more recently, with special emphasis on application of arylhydrazine, arylamine, nitroarene, azoxyarene, arylazide, and their derivatives.

Cite this article

Qin Chuanguang , Li Yang , Li Hailiang , Li Dawei , Niu Weining , Shang Xiaoya , Xu Chunlan . Novel Progresses in Synthesis Strategies of Aromatic Azo Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 444 -457 . DOI: 10.6023/cjoc201209042

References

[1] Cannizzo, C.; Amigoni-gerbier, S.; Frigoli, M.; Larpent C. J. Polym. Sci.: Part A: Polym. Chem. 2008, 6, 3375.

[2] Brenzovich, Jr., E. W.; Houk, J. T. R.; Malubay, M. A. S.; Miranda, O. J.; Ross, M. K.; Abelt, J. C. Dyes Pigm. 2002, 52, 101.

[3] Athey Jr., R. D. Eur. Coat. J. 1998, 3, 146.

[4] Sandborn, W. J. Am. J. Gastroenterol. 2002, 97, 2939.

[5] (a) Jain, A.; Gupta, Y.; Jain, S. K. Crit. Rev. Ther. Drug Carrier Syst. 2006, 23, 349.
(b) Mei, X.; Yang, S.; Chen, D. Y.; Li, N. J.; Li, H.; Xu, Q. F.; Ge, J. F.; Lu, J. M. Chem. Commun. 2012, 48, 9846.

[6] Cisnetti, F.; Ballardini, R.; Credi, A.; Gandolfi, M. T.; Masiero, S.; Negri, F.; Pieraccini, S.; Spada G. P. Chem.-Eur. J. 2004, 10, 2011.

[7] (a) Li, W. W.; Xu, D. M.; Zhang, Z. L.; Xu, Y. Chin. J. Chem. 2012, 30, 1819.
(b) Natansohn, A.; Rochon, P. Chem. Rev. 2002, 102, 4139.

[8] Lee, K. M.; Wang, H. D.; Koerner, H.; Vaia, A. R.; Tan, L.-S.; White J. T. Angew. Chem., Int. Ed. 2012, 51, 4117.

[9] Deloncle, R.; Caminade, A.-M. J. Photochem. Photobiol. C: Photochem. Rev. 2010, 11, 25.

[10] (a) Bandara, D.; Burdette, C. S. Affiliation Information . University of Connecticut, 55 North Eagleville Road, Storrs, USA Chem. Soc. Rev. 2012, 41, 1809.
(b) Ikeda, T.; Tsutsumi, O. Science 1995, 268, 1873.

[11] Tamaoki, N. Adv. Mater. 2001, 13, 1135.

[12] Feringa, B. L.; Van Delden, R. A.; Koumura, N.; Geertsema, E. M. Chem. Rev. 2000, 100, 1789.

[13] (a) Wegner, A. H. Angew. Chem., Int. Ed. 2012, 51, 4787.
(b) Beharry, A. A.; Woolley, G. A. Chem. Soc. Rev. 2011, 40, 4422.
(c) Hoppmann, C.; Seedorff, S.; Richter, A.; Fabian, H.; Schmieder, P. Angew. Chem., Int. Ed. 2009, 48, 6636.
(d) Gorostiza1, P.; Isacoff, Y. E. Science 2008, 322, 395.

[14] Beharry, A. A.; Wong, L.; Tropepe, V.; Woolley, G. A. Angew. Chem., Int. Ed. 2011, 50, 1325.

[15] Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kutinake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605.

[16] Banerjee, I. A.; Yu, L.; Matsui, H. J. Am. Chem. Soc. 2003, 125, 6542.

[17] Crano, J. C.; Guglielmetti, R. Organic Photochromic and Thermochromic Compounds, Plenum Press, New York, 1999.

[18] (a) Bandara, H. M. D.; Burdette, C. S. Chem. Soc. Rev. 2012, 41, 1809.
(b) Muraoka, T.; Kinbara, K.; Aida, T. Nature 2006, 440, 512.

[19] Liang, X.; Asanuma, H.; Komiyama, M. J. Am. Chem. Soc. 2002, 124, 1877.

[20] Zhen, W.; Han, H.; Anguiano, M.; Lemere, C.; Cho, C.-G.; Lansbury, P. T. J. Med. Chem. 1999, 42, 2805.

[21] Barth, M.; Tasadaque, S.; Shah, A.; Rademann, J. Tetrahedron 2004, 60, 8703.

[22] Samanta, S.; Qin, C. G.; Lough, J. A.; Woolley, G. A. Angew. Chem., Int. Ed. 2012, 51, 6452.

[23] Hyatt, J. A. Tetrahedron Lett. 1977, 18, 141.

[24] Drug, E.; Gozin, M. J. Am. Chem. Soc. 2007, 129, 13784.

[25] Niu, Y.-S.; Li, J.-P; Zheng, P.-Z. Chem. Reag. 2006, 28, 109 (in Chinese).
(牛永生, 李建平, 郑鹏志, 化学试剂, 2006, 28, 109.)

[26] Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979.

[27] Kang, H. M.; Kim, H. Y.; Jung, J. W.; Cho, C. G. J. Org. Chem. 2007, 72, 679.

[28] Dohno, C.; Yamamoto, T.; Nakatani, K. Eur. J. Org. Chem. 2009, 4051.

[29] Kim, K. Y.; Shin, J. T.; Lee, K. S.; Cho, C. G. Tetrahedron Lett. 2004, 45, 117.

[30] Smith, L. I.; Irvine, W. B. J. Am. Chem. Soc. 1941, 63, 1036.

[31] Hecker, E.; Lattrell, R. Justus Liebigs Ann. Chem. 1963, 662, 48.

[32] Taylor, E. C.; Jagdmann, Jr. G. E.; McKillop, A. J. Org. Chem. 1978, 43, 4385.

[33] Naemura, K.; Wanebe, T.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1997, 8, 873.

[34] Carreno, C. M.; Fernandez-Mudarra, G.; Merino, E.; Ribagorda, M. J. Org. Chem. 2004, 69, 3413.

[35] Carreno, C. M.; Garcia, I.; Ribagorda, M.; Merino, E.; Pieraccini, S.; Spada, G. P. Org. Lett. 2005, 7, 2869;

[36] Carreno, C. M.; Garcia, I.; Nunez, I.; Merino, E.; Ribagorda, M.; Pieraccini, S.; Spada, G. P. J. Am. Chem. Soc. 2007, 129, 7089.

[37] Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. 1997, 36, 2550.

[38] Patel, S.; Mishra, B. K. Tetrahedron Lett. 2004, 45, 1371.

[39] Noureldin, N. A.; Bellegarde, J. W. Synthesis 1999, 939.

[40] Karunakaran, C.; Palanisamy, P. N. J. Mol. Catal. A: Chem. 2001, 172, 9.

[41] Orito, K.; Hatakeyama, T.; Takeo, M.; Uchiito, S.; Tokuda, M.; Suginome, H. Tetrahedron 1998, 54, 8403.

[42] Farhadi, S.; Zaringhadam, P.; Sahamieh, R. Z. Acta Chim. Slov. 2007, 54, 647.

[43] (a) Chi, L.; Sadovski, O.; Woolley, G. A. Bioconjugate Chem. 2006, 17, 670.
(b) Gilbert, M. A.; Failli, A.; Shumsky, J.; Yang, Y. J.; Severin, A.; Singh, G.; Hu, W. J. Med. Chem. 2006, 49, 6027.
(c) Norikane, Y.; Tamaoki, N. Org. Lett. 2004, 6(15), 2595.

[44] Gomy, C.; Schmitzer, R. A. Org. Lett. 2007, 9(20), 3865.

[45] Sadovski, O.; Beharry, A. A. Zhang, F. Z.; Woolley, G. A. Angew. Chem., Int. Ed. 2009, 48, 1484.

[46] (a)Grirrane, A.; Corma, A.; Garcia, H. Science 2008, 322, 1661.
(b) Esdaile, J. L.; Jensen, P.; McMurtrie, C. J.; Arnold, P. D. Angew. Chem., Int. Ed. 2007, 46, 2090.
(c) Leyva, E.; Medina, C.; Moctezuma, E.; Leyva, S. Can. J. Chem. 2004, 82, 1712.

[47] Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174.

[48] Shaieb, E. K.; Narayanan, V.; Hopf, H. Eur. J. Org. Chem. 2003, 567.

[49] Burns, C. D.; Zhang, F. Z; Woolley, G. A. Nat. Protoc. 2007, 2, 251.

[50] Zhang, F. Z.; Sadovski, O.; Woolley, G. A. ChemBioChem 2008, 9, 2147.

[51] Beharry, A. A.; Sadovski, O.; Woolley, G. A. Org. Biomol. Chem. 2008, 6, 4323.

[52] Samanta, S.; Woolley G. A. ChemBioChem 2011, 12, 1712.

[53] Takeda, Y.; Okumura, S.; Minakata, S. Angew. Chem., Int. Ed. 2012, 51, 7804.

[54](a) Renner, C.; Kusebauch, U.; Loweneck, M.; Milbradt, A. G.; Moroder, L. J. Pep. Res. 2005, 65, 4.
(b) Li, Y. C.; Li, S. H.; Qi, C.; Zhang, H. J.; Zhu, M. Y.; Pang, S. P. Acta Chim. Sinica 2011, 69, 2159 (in Chinese).
(李玉川, 李生华, 祁才, 张慧娟, 朱梦宇, 庞思平, 化学学报, 2011, 69, 2159.)

[55] (a) Gowenlock, B. G.; Richter-Addo, G. B. Chem. Rev. 2004, 104, 3315.
(b) Defoin, A. Synthesis 2004, 706.

[56] Yu, B. C.; Shirai, Y.; Tour, J. M. Tetrahedron 2006, 62, 10303.

[57] Tie, C.; Gallucci, J. C.; Parquette, J. R. J. Am. Chem. Soc. 2006, 128, 1162.

[58] Berryman, B. O.; Sather, C. A.; Rebek Jr., J. Chem. Commun. 2011, 47(2), 656.

[59] Kubitschke, J.; Näther, C.; Herges, R. Eur. J. Org. Chem. 2010, 5041.

[60](a) Norikane, Y.; Kitamoto, K.; Tamaoki, N. Org. Lett. 2002, 4(22), 3907.
(b) Wei, W. H.; Tomohiro, T.; Kodaka, M.; Okuno, H. J. Org. Chem. 2000, 65, 8979.

[61] Khan, A.; Hecht, S. Chem.-Eur. J. 2006, 12, 4764.

[62] Wada, S.; Urano, M.; Suzuki, H. J. Org. Chem. 2002, 67, 8254.

[63] Laskar, D. D.; Prajapati, D.; Shandu, J. S. J. Chem. Soc., Perkin Trans. 1 2000, 67.

[64] Gowda, S.; Gowda, D. C. Synthesis 2002, 460.

[65] Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Aust. J. Chem. 2004, 57, 609.

[66] Pasha, M. A.; Jayashankara, V. P. Ultrason. Sonochem. 2005, 12, 433.

[67] Stolarczyk, K.; Bilewick, R.; Skwierawska, A.; Biernat, J. F. J. Inclusion Phenom. Macrocyclic Chem. 2004, 49, 173.

[68](a)Peng, Y.; Zhao, Z.-G.; Yang, Z.-X.; Mu, Q.-M.; Chen, S.-H. Chin. J. Org. Chem. 2005, 25, 462 (in Chinese).
(彭游, 赵志刚, 杨祖幸, 牟其明, 陈淑华, 有机化学, 2005, 25, 462.)
(b) Altomare, A.; Ciardelli, F.; Marchini, M.; Solaro, R. Polymer 2005, 46, 2086.
(c) Xiong, C.-X.; Niu, Y.-S.; Zhou, W.; Dong, L.-J. J. Chem. Res. 2006, (2), 139.

[69] Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Tetrahedron Lett. 2003, 44, 5835.

[70] Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Synth. Commun. 2003, 33, 4221.

[71] Huang, Q. M.; Pan, W.; Li, Q.; Wang, S. W.; Li, Z. Y.; Pan, Z. Q. Chin. J. Org. Chem. 2011, 31, 336 (in Chinese).
(黄齐茂, 潘威, 李清, 王司卫, 李志远, 潘志权, 有机化学, 2011, 31, 336.)

[72] Won, S.; Kim, W.; Kim, H. Bull. Korean Chem. Soc. 2006, 27, 195.

[73] Sakai, N.; Fujii, K.; Nabeshima, S.; Ikeda, R.; Konakahara, T. Chem. Commun. 2010, 46, 3173.

[74] Zhu, H.; Ke, X.; Yang, X.; Sarina, S.; Liu, H. Angew. Chem., Int. Ed. 2010, 49, 9657.

[75] Shimao, I.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 643.

[76] Yamamoto, J.; Nishigaki, Y.; Umezu, M. Tetrahedron 1980, 36, 3177.

[77] Vozza, J. F. J. Org. Chem. 1969, 34, 3219.

[78] Olsen, H.; Snyder, J. P. J. Am. Chem. Soc. 1977, 99, 1524.

[79] Nanjundaswamy H. M.; Pasha, M. A. Synth. Commun. 2005, 35, 2163.

[80] Nanjundaswamy, H. M.; Pasha, M. A. Indian J. Chem. 2006, 45B, 1086.

[81] Konwar, D.; Boruah, R. C.; Sandhu, J. S. Synthesis 1990, 337.

[82] Ilias, M.; Barman, D. C.; Prajapati, D.; Sandhu, J. S. Tetrahedron Lett. 2002, 43, 1877.

[83] Saini, A.; Kumar, S.; Sandhu, J. S. Synlett 2006, 395.

[84] Baik, W.; Kim, D. I.; Koo, S.; Rhee, J. U.; Shin, S. H.; Kim, B. H.Tetrahedron Lett. 1997, 38, 845.

[85] Sanz, R.; Escribano, J.; Fernandez, Y.; Aguado, R.; Pedrosa, M. R.; Arnáiz, F. J. Synlett 2005, 1389.

[86] Olah, G. A.; Balaram Gupta, B. G.; Narang, S. C. J. Org. Chem. 1978, 43, 4503.

[87] Mukaiyama, T.; Nambu, H.; Okamoto, M. J. Org. Chem. 1962, 27, 3651.

[88] Scriven, E. F. V.; Suschitzky, H. Tetrahedron Lett. 1973, 14, 103.

[89] Mankad, P. N.; Muller, P.; Peters, C. J. J. Am. Chem. Soc. 2010, 132, 4083.

[90] Takaoka, A.; Moret, M.-E.; Peters, C. J. J. Am. Chem. Soc. 2012, 134, 6695.

[91] Haghbeen, K.; Tan, E. W. J. Org. Chem. 1998, 63, 4503.

[92] Wang, S.-R.; Li, X.-G; He, L.-L.; Hu, Y.-Q. J. Tianjin Univ. 2007, 40, 1295 (in Chinese).
(王世荣, 李祥高, 何莉莉, 胡雅琴, 天津大学学报, 2007, 40, 1295.)

[93] Xu, L. J.; Lin, W. H.; Sun, W. L.; Shen, Z. Q. Acta Polym. Sin. 2008, 1, 62 (in Chinese).
(徐磊杰, 林维红, 孙维林, 沈之荃, 高分子学报, 2008, 1, 62.)

[94] Han, M.; Ishikawa, D.; Muto, E.; Hara, M. J. Lumines 2009, 129, 1163.

[95] Feng, F.; Hu, W. B.; Liu, H. X.; Nie, X. L.; Yu, A. N. Chin. J. Appl. Chem. 2010, 27, 169 (in Chinese).
(冯驸, 胡卫兵, 刘红霞, 聂响亮, 余爱农, 应用化学, 2010, 27, 169.)

[96] Liu, G.; Zhang, B.; Chen, Y.; Zhu, C.-X.; Zeng, L. J.; Chan, D. S.-H.; Neoh, K.-G.; Kang, E.-T. J. Mater. Chem. 2011, 21, 6027.

[97] Merrington, J.; James, M.; Bradley, M. Chem. Commun. 2002, 38, 140.

[98] Kim, J. Y.; Kim, G.; Kim, C. R.; Lee, S. H.; Lee, J. H.; Kim, J. S. J. Org. Chem. 2003, 68, 1933.

[99] Barbero, M.; Degani, I.; Dughera, S.; Fochi, R.; Perracino, P. Synthesis 1998, 1235.
[100] Merino, E. Chem. Soc. Rev. 2011, 40, 3835.
Outlines

/