硫氰酸酯类化合物的合成及其应用研究进展
收稿日期: 2018-07-08
修回日期: 2018-08-27
网络出版日期: 2018-09-18
基金资助
绍兴文理学院校级科研（No.2017LG1001）资助项目.
Progress on the Synthesis and Applications of Thiocyanates
Received date: 2018-07-08
Revised date: 2018-08-27
Online published: 2018-09-18
Supported by
Project supported by the Research Project of Shaoxing University (No. 2017LG1001).
徐庆 , 张连阳 , 冯高峰 , 金城安 . 硫氰酸酯类化合物的合成及其应用研究进展[J]. 有机化学, 2019 , 39(2) : 287 -300 . DOI: 10.6023/cjoc201807016
Thiocyanates (RSCN) are important synthetic intermediates, which have been widely used for the synthesis of pesticides, medicines and materials. In recent years, great advances in the synthesis and transformations of this class of compounds have been made, and many synthetic applications of those compounds have been emerged. In this review, the synthetic methods and transformations of thiocyanates are introduced systematically, which may provide assistance for the studies of thiocyanates in this area.
Key words： thiocyanates; synthetic methods; application
[1] Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujvary, I.; Szajnman, S. H.; Rodriguez, J. B. J. Med. Chem. 2002, 45, 3984.
[2] Kokorekin, V. A.; Terent'ev, A. O.; Ramenskaya, G. V.; Gram-matikova, N. E.; Rodionava, G. M.; llovaiskii, A. I. Pharm. Chem. J. 2013, 47, 422.
[3] Dutta, S.; Abe, H.; Aoyagi, S.; Kibayashi, C.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 15004.
[4] Capon, R. J.; Skene, C.; Liu, E. H.-T.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Org. Chem. 2001, 66, 7765.
[5] Yasmana, Y.; Edrada, R. A.; Wray, V.; Proksch, P. J. Nat. Prod. 2003, 66, 1512.
[6] Billard, T.; Large, S.; Langlois, B. R. Tetrahedron Lett. 1997, 38, 65.
[7] Johnson, T. B.; Douglass, I. B. J. Am. Chem. Soc. 1939, 61, 2548.
[8] Sabacky, M. J.; Johnson, S. M.; Martin, J. C.; Paul, I. C. J. Am. Chem. Soc. 1969, 91, 7542.
[9] Aureggi, V.; Sedelmeier, G. Angew. Chem. Int. Ed. 2007, 46, 8440.
[10] Ciszek, J. W.; Stewart, M. P.; Tour, J. M. J. Am. Chem. Soc. 2004, 126, 13172.
[11] Still, I. W. J.; Toste, F. D. J. Org. Chem. 1996, 61, 7677.
[12] Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494.
[13] Sun, N.; Che, L.-S.; Mo, W.-M.; Hu, B.-X.; Shen, Z.-L.; Hu, X.-Q. Org. Biomol. Chem. 2015, 13, 691.
[14] Zhu, N.; Wang, F.; Chen, P.-H.; Ye, J.-X.; Liu, G.-S. Org. Lett. 2015, 17, 3580.
[15] Jiang, H.-F.; Yu, W.-T.; Tang, X.-D.; Li, J.-X.; Wu, W.-Q. J. Org. Chem. 2017, 82, 9312.
[16] Chen, Y.-T.; Wang, S.-F.; Jiang, Q.-W.; Cheng, C.-G.; Xiao, X.-H.; Zhu, G.-G. J. Org. Chem. 2018, 83, 716.
[17] Rad, M. N. S. J. Chem. Res. 2016, 40, 583.
[18] Dwivedi, V.; Rajesh, M.; Kumar, R.; Kantc, R.; Reddy, M. S. Chem. Commun. 2017, 53, 11060.
[19] Palsuledesai, C. C.; Murru, S.; Sahoo, S. K.; Patel, B. K. Org. Lett. 2009, 11, 3382.
[20] Modi, A.; Ali, W.; Patel, B. K. Org. Lett. 2017, 19, 432.
[21] Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696.
[22] Zhang, D.; Wang, H.; Bolm, C. Chem. Commun. 2018, 54, 5772.
[23] Liang, S.; Zeng, C.-C.; Tian, H.-Y.; Sun, B.-G.; Luo, X.-G.; Ren, F.-Z. Adv. Synth. Catal. 2018, 360, 1444.
[24] Xiong, H.-Y.; Pannecoucke, X.; Besset, T. Org. Chem. Front. 2016, 3, 620.
[25] Zhang, H.-L.; Wei, Q.; Wei, S.-Q.; Qu, J.-P.; Wang, B.-M. Eur. J. Org. Chem. 2016, 20, 3373.
[26] Chen, Q.; Lei, Y.-J.; Wang, Y.-F.; Wang, C.; Wang, Y.-N.; Xu, Z.-Q.; Wang, H.; Wang, R. Org. Chem. Front. 2017, 4, 369.
[27] Wang, Z.-H.; Wang, L.; Chen, Q.; He, M.-Y. Synth. Commun. 2018, 40, 76.
[28] Venkanna, P.; Rajanna, K. C.; Kumar, M. S.; Venkateswarlu, M.; Ali, M. M. Synlett 2016, 27, 237.
[29] Qiu, J.-S.; Wu, D.; Karmaker, P. G.; Yin, H.-Q.; Chen, F.-X. Org. Lett. 2018, 20, 1600.
[30] Wu, D.; Qiu, J.-S.; Karmaker, P. G.; Yin, H.-Q.; Chen, F.-X. J. Org. Chem. 2018, 83, 1576.
[31] Yang, H.; Duan, X.-H.; Zhao, J.-F.; Guo, L.-N. Org. Lett. 2015, 17, 1998.
[32] Yang, D.-S.; Yan, K.-L.; Wei, W.; Li, G.-Q.; Lu, S.-L.; Zhao, C.-X.; Tian, L.-J.; Wang, H. J. Org. Chem. 2015, 80, 11073.
[33] Zhang, X.-Z.; Ge, D.-L.; Chen, S.-Y.; Yu, X.-Q. RSC Adv. 2016, 6, 66320.
[34] Guo, L.-N.; Gu, Y.-R.; Yang, H.; Hu, J. Org. Biomol. Chem. 2016, 14, 3098.
[35] Chen, J.-C.; Wang, T.-Y.; Wang, T.; Lin, A.-J.; Yao, H.-Q.; Xu, J.-Y. Org. Chem. Front. 2017, 4, 130.
[36] Mete, T. B.; Khopade, T. M.; Bhat, R. G. Tetrahedron Lett. 2017, 58, 415.
[37] Ji, F.; Fan, Y.; Yang, R.; Yang, Y.-Y.; Yu, D.-W.; Wang, M.-Y.; Li, Z.-Y. Asian J. Org. Chem. 2017, 6, 682.
[38] Karmaker, P. G.; Qiu, J.; Wu, D.; Yin, H.; Chen, F. X. Synlett 2018, 29, 954.
[39] Zeng, Y.-F.; Tan, D.-H.; Chen, Y.-Y.; Lv, W.-X.; Liu, X.-G.; Li, Q.-J.; Wang, H.-G. Org. Chem. Front. 2015, 2, 1511.
[40] Lv, Y.-H.; Pu, W.-Y.; Cui, H.; He, J.-L.; Zhang, Q.-M. Synth. Commun. 2016, 46, 1223.
[41] Tao, Z.-K.; Li, C.-K.; Zhang, P.-Z.; Shoberu, A.; Zou, J.-P.; Zhang, W. J. Org. Chem. 2018, 83, 2418.
[42] Fan, W.-G.; Yang, Q.; Xu, F.-S.; Li, P.-X. J. Org. Chem. 2014, 79, 10588.
[43] Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275.
[44] Wang, L.; Wang, C.-C.; Liu, W.-J.; Chen, Q.; He, M.-Y. Tetrahedron Lett. 2016, 57, 1771.
[45] Singh, M.; Yadav, A. K.; Yadav, L. D. S.; Singh, R. K. P. Synlett 2018, 29, 176.
[46] Li, W.; Yang, C.; Gao, G.-L.; Xia, W.-J. Chin. J. Org. Chem. 2017, 37, 480(in Chinese). (李伟, 杨超, 高国林, 夏吾炯, 有机化学, 2017, 37, 480.)
[47] Castanheiro, T.; Gulea, M.; Donnard, M.; Suffert, J. Eur. J. Org. Chem. 2014, 7814.
[48] Guo, W.; Tan, W.; Zhao, M.; Zheng, L.; Tao, K.; Chen, D.; Fan, X. J. Org. Chem. 2018, 83, 6580.
[49] Frei, R.; Courant, T.; Wodrich, M. D.; Waser, J. Chem.-Eur. J. 2014, 20, 1.
[50] Zhu, D.; Chang, D.-H.; Shi, L. Chem. Commun. 2015, 51, 7180.
[51] Teng, F.; Yu, J.-T.; Yang, H.-T.; Jiang, Y.; Cheng, J. Chem. Commun. 2014, 50, 12139.
[52] Wang, Z.-H.; Ji, X.-M.; Hu, M.-L.; Tang, R.-Y. Tetrahedron Lett. 2015, 56, 5067.
[53] Linderoth, L.; Fristrup, P.; Hansen, M.; Melander, F.; Madsen, R.; Andresen, T. L.; Peters, G. H. J. Am. Chem. Soc. 2009, 131, 12193.
[54] Brown, S. P.; Smith, A. B. Ⅲ J. Am. Chem. Soc. 2015, 137, 4034.
[55] Ke, F.; Qu, Y.-Y.; Jiang, Z.-Q.; Li, Z.-K.; Wu, D.; Zhou, X.-G. Org. Lett. 2011, 13, 454.
[56] Hajipour, A. R.; Pourkaveh, R.; Karimi, H. Appl. Organomet. Chem. 2014, 28, 879.
[57] Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 1716.
[58] Lu, X.-G.; Wang, H.-M.; Gao, R.-L.; Sun, D.-M.; Bi, X.-J. RSC Adv. 2014, 4, 28794.
[59] Bisogno, F. R.; Cuetos, A.; Lavandera, I.; Gotor, V. Green Chem. 2009, 11, 452.
[60] Sano, T.; Takagi, T.; Gama, Y.; Shibuya, I.; Shimizu, M. Syn-thesis 2004, 1585.
[61] Wang, F.; Chen, C.; Deng, G.; Xi, C.-J. J. Org. Chem. 2012, 77, 4148.
[62] Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3908.
[63] Roh, J.; Artamonova, T. V.; Vavrova, K.; Koldobskii, G. I.; Hrabalek, A. Synthesis 2009, 2175.
[64] Roh, J.; Vavrova, K.; Hrabalek, A. Eur. J. Org. Chem. 2012, 31, 6101.
[65] Yoneyama, H.; Usami, Y.; Komeda, S.; Harusawa, S. Synthesis 2013, 45, 1051.
[66] Vorona, S.; Artamonova, T.; Zevatskii, Y.; Myznikov, L. Syn-thesis 2014, 46, 781.
[67] Marshall, W. S.; Caruthers, M. H. Science 1993, 259, 1564.
[68] Cieslak, J.; Jankowska, J.; Stawinski, J.; Kraszewski, A. J. Org. Chem. 2000, 65, 7049.
[69] Renard, P.-Y.; Schwebel, H.; Vayron, P.; Josien, L.; Valleix, A.; Mioskowski, C. Chem.-Eur. J. 2002, 8, 2910.
[70] Jansa, P.; Cechova, L.; Dracínsky, M.; Janeba, Z. RSC Adv. 2013, 3, 2650.
[71] Gonda, J.; Martinková, M.; Raschmanová, J.; Balentová, E. Tetrahedron:Asymmetry 2006, 17, 1875.
[72] Sundermeier, M.; Zapf, A.; Beller, M.; Sans, S. Tetrahedron Lett. 2001, 42, 6707.
[73] Zhang, Z.-H.; Liebeskind, L. S. Org. Lett. 2006, 8, 4331.
[74] Lee, Y. T.; Choi, S. Y.; Chung, Y. K. Tetrahedron Lett. 2007, 48, 5673.
[75] Potash, S.; Rozen, S. J. Fluorine Chem. 2014, 168, 173.
[76] Jouvin, K.; Matheis, C.; Goossen, L. J. Chem.-Eur. J. 2015, 21, 14324.
/
| 〈 |
|
〉 |
