Chinese Journal of Organic Chemistry >
Construction of Nitrogen-Oxygen-Heterocycles via Copper-Free Click Reactions of Nitrile Oxides
Received date: 2013-11-26
Revised date: 2014-01-11
Online published: 2014-02-10
Supported by
Project supported by the National Natural Science Foundation of China (No. 21004024), the Natural Science Foundation of Fujian Province (No. 2011J01046), the Program for New Century Excellent Talents in Fujian Province (No. 2012FJ-NCET-ZR03), the University Distinguished Young Research Talent Training Program of Fujian Province (No. 11FJPY02) and the Promotion Program for Young and Middle-aged Teacher in Science and Technology Research of Huaqiao University (No. ZQN-YX103).
Click chemistry has been developed rapidly, which was initially proposed by Sharpless and co-workers since 2001. As the representative of click chemistry, the Cu(I)-catalyzed azide-alkyne cycloaddition (Cue-AAC) reaction has been applied widely for the preparation of new materials, drugs and catalyst carriers. The copper metal contamination in the final products is a major concern because of the use of copper salts catalytic system. These drawbacks counteract their applications in the fields of biomedicine and pharmaceuticals. Click reactions based on nitrile oxides with the feature of copper-free catalysis, not only can produce isoxazoles and isoxazolines by reacting with nitrile oxides and alkynes/alkenes, but also can synthesize oxadiazoles from nitrile oxides and nitriles. Copper-free nitrile oxides click reactions have good region- and stereo-selective properties and have been applied to the synthesis of drugs and bioactive compounds with particular structures. The new progress of click reactions based on nitrile oxide is reviewed.
Key words： click chemistry; nitrile oxides; alkynes; alkenes; nitriles; copper-free catalysis
Han Qian , Yi Chao , Xiong Xingquan . Construction of Nitrogen-Oxygen-Heterocycles via Copper-Free Click Reactions of Nitrile Oxides[J]. Chinese Journal of Organic Chemistry, 2014 , 34(6) : 1092 -1103 . DOI: 10.6023/cjoc201311044
[1] Michael, A.; Luehn, F.; Higbee, H. H. Am. Chem. J. 1898, 20, 377.
[2] Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565.
[3] Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
[4] Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem., 2002, 67, 3057.
[5] Morten, M.; Christian, W. T. Chem. Rev. 2008, 108, 2952.
[6] Wang, Q.; Hawker, C. Chem. Asian J. 2011, 6, 2568.
[7] Xiong, X. Q.; Cai, L.; Tang, Z. K. Chin. J. Org. Chem. 2012, 32, 1410 (in Chinese).
(熊兴泉, 蔡雷, 唐忠科, 有机化学, 2012, 32, 1410.)
[8] Mamidyala, S. K.; Finn, M. G. Chem. Soc. Rev. 2010, 39, 1252.
[9] Aragao-Leoneti, V.; Campo, V. L.; Gomes, A. S.; Field, R. A.; Carvalho, I. Tetrahedron 2010, 66, 9475.
[10] Cao, J.; Huang, X. J. Comb. Chem. 2008, 10, 526.
[11] Meldal, M. Macromol. Rapid Commun. 2008, 29, 1016.
[12] Golas, P. L.; Matyjaszewski, K. Chem. Soc. Rev. 2010, 39, 1338.
[13] Lutz, J. F. Angew. Chem., Int. Ed. 2007, 46, 1018.
[14] Chow, H. F.; Lau, K.-N.; Ke, Z.; Liang, Y.; Lo, C.-M. Chem. Commun. 2010, 46, 3437.
[15] Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262.
[16] Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620.
[17] Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639.
[18] Brewer, J. G. Chem. Res. Toxicol. 2010, 23, 319.
[19] Ornelas, C.; Aranzaes, J. R.; Cloutet, E.; Alves, S.; Astruc, D. Angew. Chem., Int. Ed. 2007, 46, 872.
[20] Hong, J.; Luo, Q.; Shah, B. K. Biomacromolecules 2010, 11, 2960.
[21] Lee, Y. G.; Yonekawa, M.; Koyama, Y.; Takata, T. Chem. Lett. 2010, 39, 420.
[22] Vaidya, V. V.; Wankhede, K. S.; Nara, S. J.; Salunkhe, M. M.; Trivedi, G. K. Synth. Commun. 2009, 39, 3856.
[23] Bigdeli, M. A.; Halimehjani, A. Z.; Mohammadipour, M.; Sagharichi, P. J. Heterocycl. Chem. 2012, 49, 926.
[24] Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
[25] Sanders, B. C.; Friscourt, F.; Ledin, P. A.; Mbua, N. E.; Arumugam, S.; Guo, J.; Boltje, T. J.; Popik, V. V.; Boons, G.-J. J. Am. Chem. Soc. 2011, 133, 949.
[26] Li, H. M. M.S. Thesis, Jilin University, Jilin, 2012 (in Chinese).
(李洪明, 硕士论文, 吉林大学, 吉林, 2012.)
[27] Claisen, L.; Lowman, O. E. Ber. Dtsch. Chem. Ges. 1888, 21, 784.
[28] Kumar, A.; Maruya, R. A.; Sharma, S.; Ahmad, P.; Singh, A. B.; Tamrakar, A. K.; Srivastava, A. K. Bioorg. Med. Chem. 2009, 17, 5285.
[29] Wang, Y. G.; Xu, W. M.; Huang, X. Synthesis 2007, 28.
[30] Praveen, C.; Kalyanasundaram, A.; Perumal, P. T. Synlett 2010, 777.
[31] Mazzei, M.; Balbi, A.; Sottofattori, E.; Garzoglio, R.; Montis, A. D.; Corrias, S.; Colla. P. L. Eur. J. Med. Chem. 1993, 28, 669.
[32] Yokoyama, M.; Tsujiand, K.; Kushida, M. J. Chem. Soc., Perkin Trans. 1 1986, 67.
[33] Zen, S.; Harada, K.; Nakamura, H.; Iitaka, Y. Bull. Chem. Soc. Jpn. 1988, 61, 2881.
[34] Tang, S.; He, J.; Sun, Y.; He, L.; She, X. Org. Lett. 2009, 11, 3982.
[35] Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203.
[36] Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643.
[37] Jawalekar, A M.; Reubsaet, E.; Rutjes, F. P. J. T.; Van Delft, F. L. Chem. Commun. 2011, 47, 3198.
[38] Singh, I.; Heaney, F. Org. Biomol. Chem. 2010, 8, 451.
[39] Lugi?ina, J.; Rjabovs, V.; Belyakov, S.; Turks, M. Tetrahedron Lett. 2013, 54, 5328.
[40] Basappa; Sadashiva, M. P.; Mantelingu, K.; Swamy, S. N.; Rangappa, K. E. Bioorg. Med. Chem. 2003, 11, 4539.
[41] Pirrung, M. C.; Tumey, L. N.; Raetz, C. R. H.; Jackman, J. E.; Snehalatha, K.; McClerren, A. L.; Fierke, C. A.; Gantt, S. L.; Rusche, K. M. J. Med. Chem. 2002, 45, 4359.
[42] Majumder, S.; Bhuyan, P. J. Tetrahedron Lett 2012, 53, 762.
[43] Nonn, M.; Kiss, L.; Sillanpää, R.; Fülöp, F. Tetrahedron 2012, 68, 9942
[44] Chittimalla, S. K.; Kuppusamy, R.; Thiyagarajan, K.; Bandi, C. Eur. J. Org. Chem. 2013, 13, 2715.
[45] Quadrelli, P.; Mella, M.; Legnani, L.; Al-Saad, D. Eur. J. Org. Chem. 2013, 13, 4655.
[46] Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Sriram, D. Eur. J. Med. Chem. 2012, 53, 416.
[47] Kumar, R. S.; Ramar, A.; Perumal, S.; Almansour, A. I.; Arumugam, N.; Ali, M. A. Synth. Commun. 2013, 43, 2763.
[48] Lee, Y. G.; Koyama, Y.; Yonekawa, M.; Takata, T. Macromolecules 2010, 43, 4070.
[49] Matsumura, T.; Ishiwari, F.; Koyama, Y.; Takata, T. Org. Lett. 2010, 12, 3828.
[50] Jang, K.; Miura, K.; Koyama, Y.; Takata, T. Org. Lett. 2012, 14, 3088.
[51] Yuki, T.; Koyama, Y.; Matsumura, T.; Takata, T. Org. Lett. 2013, 15, 4438.
[52] Iguchi, H.; Uchida, S.; Koyama, Y.; Takata, T. ACS Macro Lett. 2013, 2, 527.
[53] Iwakura, Y.; Shiraishi, S.; Akiyama, M.; Yuyama, M. Bull. Chem. Soc. Jpn. 1968, 41, 1648.
[54] Iwakura, Y.; Uno, K.; Hong, S.-J.; Hongu, T. Polym. J. 1971, 2, 36.
[55] Koyama, Y.; Yonekawa, M.; Takata, T. Chem. Lett. 2008, 37, 918.
[56] Lee, Y. G.; Koyama, Y.; Yonekawa, M.; Takata, T. Macromolecule 2009, 42, 7709.
[57] Koyama, Y.; Miura, K.; Cheawchan, S.; Seo, A.; Takata, T. Chem. Commun. 2012, 48, 10304.
[58] Ledin, H. H., Kolishetti, N.; Boons, G. J. Macromolecules 2013, 46, 7759.
[59] Wu, G.-J.; Sheng, S.-R.; Li, D.; Xu, L.-F.; Huang, Z.-Z. Synth. Commun. 2013, 43, 3034.
[60] Cheawchan, S.; Koyama, Y.; Uchida, S.; Takata, T. Polymer 2013, 54, 4501.
[61] Gutsmiedl, K.; Wirges, C. T.; Ehmke, V.; Carell, T. Org. Lett. 2009, 11, 2405.
[62] Singh, I.; Vyle, J. S.; Heaney, F. Chem. Commun. 2009, 45, 3276.
[63] Singh, I.; Heaney, F. Chem. Commun. 2011, 47, 2706.
[64] Gutsmiedl, K.; Fazio, D.; Carell, T. Chem. Eur. J. 2010, 16, 6877.
[65] Singh, I.; Zarafshani, Z.; Heaney, F.; Lutz, J. F. Polym. Chem. 2011, 2, 372.
[66] Sanders, B. C.; Friscourt, F.; Ledin, P. A.; Mbua, N. E.; Arumugam, S.; Guo, J.; Boltje, T. J.; Popik, V. V.; Boons, G. J. J. Am. Chem. Soc. 2011, 133, 949.
[67] Wendeln, C.; Singh, I.; Rinnen, S.; Schulz, C.; Arlinghaus, H. F.; Burley, G. A.; Ravoo, B. J. Chem. Sci. 2012, 3, 2479.
[68] Minakata, S.; Okumura, S.; Nagamachi, T.; Takeda, Y. Org. Lett. 2011, 13, 2966.
/
| 〈 |
|
〉 |
