四正丁基碘化胺/叔丁基过氧化氢催化氧化合成噻唑啉衍生物的反应研究
收稿日期: 2017-01-22
修回日期: 2017-03-05
网络出版日期: 2017-03-08
基金资助
国家自然科学基金（No.21372137）资助项目.
Tetrabutylammonium Iodide/t-Butylhydroperoxide Catalytic/Oxidative Synthesis of Thiazolylidene Derivatives
Received date: 2017-01-22
Revised date: 2017-03-05
Online published: 2017-03-08
Supported by
Project supported by the National Natural Science Foundation of China (No.21372137).
建立了一种以β-芳甲酰硫代酰胺（KTAs）和丙二腈为合成砌块合成噻唑啉衍生物的新方法.采用廉价的四正丁基碘化胺（TBAI）/叔丁基过氧化氢（TBHP）为催化氧化体系，在三乙胺存在下，室温反应1 h得到一系列4-氨基噻唑啉衍生物.该方法具有操作简便、反应条件温和、反应时间短、后处理简单、环境友好等特点.
关键词： 噻唑啉; β-芳甲酰基硫代酰胺; TBAI/TBHP; 催化
于乐 , 刘瑞娟 , 李明 . 四正丁基碘化胺/叔丁基过氧化氢催化氧化合成噻唑啉衍生物的反应研究[J]. 有机化学, 2017 , 37(7) : 1800 -1807 . DOI: 10.6023/cjoc201701045
Two novel N-heterocyclic carbene-palladium (II) complexes were conveniently synthesized through one-pot reactions of imidazolium salts,palladium chloride and acridine.The new complexes have been fully characterized by 1H NMR,13C NMR,elemental analysis,and X-ray single-crystal diffraction.Moreover,the obtained palladium (II) complexes were the effective catalyst precursors for the Suzuki-Miyaura coupling of aryl as well as benzyl chlorides with arylboronic acids.Under the optimal conditions,all reactions proceeded successfully to give the desired products in good to almost quantitative yields.
Key words： thiazolylidenes; β-ketothioamides; TBAI/TBHP; catalysis
[1] Kashyap, S. J.; Garg, V. K.; Sharma, P. K.; Kumar, N.; Dudhe, R.; Gupta, J. K. Med. Chem. Res. 2012, 21(8), 2123.
[2] (a) Meneely, K. M.; Ronnebaum, T. A.; Riley, A. P.; Prisinzano, T. E.; Lamb, A. L. Biochemistry 2016, 55, 5423.
(b) Boyce, R. J.; Pattende, G. Tetrahedron 1995, 51(26), 7313.
[3] Carroll, W. A.; Dart, M. J.; Kolasa, T.; Meyer, M. D.; Patel, M. V.; Wang, X.-Q. WO 2008063781, 2008[Chem. Abstr. 2008, 639601]
[4] Takamizawa, A.; Harada, H. DE 2458933, 1975[Chem. Abstr. 1975, 514384]
[5] (a) Iravani, N.; Keshavarz, M.; Monfareda, M.; Hosseini, F. J. Chin. Chem. Soc. 2014, 61, 357.
(b) Yavari, I.; Hosseinpour, R.; Pashazadeh, R.; Ghanbari, E.; Skoulika, S. Tetrahedron 2013, 69, 2462.
(c) Alya, A. A.; Ishaka, E. A.; Brown, A. B. J. Sulfur Chem. 2014, 35(4), 382.
[6] (a) Wu, X.-F.; Gong, J.-L.; Qi, X.-X. Org. Biomol. Chem. 2014, 12, 5807.
(b) Hao, W.-J.; Du, Y.; Wang, D.; Jiang, B.; Gao, Q.; Tu, S.-J.; Li, G.-G. Org. Lett. 2016, 18, 1884.
(c) Liu, Z.-J.; Zhang, J.; Chen, S.-L.; Shi, E.-B.; Xu, Y.; Wan, X.-B. Angew. Chem., Int. Ed. 2012, 51, 3231.
(d) Zhang, Y.; Hu, G.-B.; Ma, D.-M.; Xu, P.-X.; Gao, Y.-X.; Zhao, Y.-F. Chem. Commun. 2016, 52, 2815.[e] Tang, Y.-C.; Zhang, M.; Li, X.-Q.; Xu, X.-S.; Du, X.-H. Chin. J. Org. Chem. 2015, 35, 875(in Chinese). (唐裕才, 张敏, 李小青, 许响生, 杜晓华, 有机化学, 2015, 35, 875.)
(f) Ma, L.-J.; Wang, X.-P.; Yu, W.; Han, B.. Chem. Commun. 2011, 47, 11333.
(g) Wang, Q.; Xu, Z. Chin. J. Org. Chem. 2013, 33, 2430(in Chinese). (王倩, 徐洲, 有机化学, 2013, 33, 2430.)
(h) Yu, H.; Chen, Y.-G.; Zhang, Y.-H. Chin. J. Chem. 2015, 33(5), 531.
(i) Yu, H.; Zhang, Y.-H. Chin. J. Chem. 2016, 34(4), 359.
[7] (a) Zhang, L.; Dong, J.-H.; Xu, X.-X.; Liu, Q. Chem. Rev. 2016, 116, 287.
(b) Pan, L.; Bi, X.-H.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251.
(c) Luo, X.-Y.; Ge, L.-S.; An, X.-L.; Jin, J.-H.; Wang, Y.; Sun, P.-P.; Deng, W.-P. J. Org. Chem. 2015, 80, 4611.
(d) Singh, M. S.; Nandi, G. C.; Samai, S. Green Chem. 2012, 14, 447.
(e) Huang, F.; Wu, P.; Wang, L.-D.; Chen, J.-P.; Sun, C.-L.; Yu, Z.-K. Chem. Commun. 2014, 50, 12479.
(f) Wen, L.-R.; He, T.; Lan, M.-C.; Li, M. J. Org. Chem. 2013, 78, 10617.
(g) Nandi, G. C.; Singh, M. S. J. Org. Chem. 2016, 81, 5824.
(h) Yugandar, S.; Konda, S.; Parameshwarappa, G.; Ila, H. J. Org. Chem. 2016, 81, 5606.
[8] Guo, W.-S.; Wen, L-R.; Li, M. Org. Biomol. Chem. 2015, 13, 1942.
[9] (a) Wen, L.-R.; Sun, J.-H.; Li, M.; Sun, E.-T.; Zhang, S.-S. J. Org. Chem. 2008, 73, 1852.
(b) Li, M.; Zuo, Z.-Q.; Wen, L.-R.; Wang, S.-W. J. Comb. Chem. 2008, 10, 436.
(c) Wen, L.-R.; Shi, Y.-J.; Liu, G.-Y.; Li, M. J. Org. Chem. 2012, 77, 4252.
(d) Li, M.; Hou, Y.-L.; Wen L.-R.; Gong, F.-M. J. Org. Chem. 2010, 75, 8522.
(e) Li, M.; Shao, P.; Wang, S.-W.; Kong, W.; Wen, L.-R. J. Org. Chem. 2012, 77, 8956.
[10] (a) Maiboroda, E. I.; Britsun, V. N. Russ. J. Org. Chem. 2008, 44, 1200.
(b) Britsun, V. N. Russ. J. Org. Chem. 2008, 44, 1528.
[11] Wen, L.-R.; Men, L.-B.; He, T.; Ji, G.-J. Li, M. Chem.-Eur. J. 2014, 20, 5028.
[12] (a) Li, M.; Cao, H.; Wang, Y.; Lv, X.-L.; Wen, L.-R. Org. Lett. 2012, 14, 3470.
(b) Li, M.; Kong, X.-J.; Wen, L.-R. J. Org. Chem. 2015, 80, 11999.
(c) Guo, W.-S.; Xin, X.; Zhao, K.-L.; Wen, L.-R.; Li, M. RSC Adv. 2015, 5, 70429.
[13] (a) Qiu, J.-K.; Hao, W.-J. Wang, D.-C.; Wei, P.; Sun, J.; Jiang, B.; Tu, S.-J. Chem. Commun. 2014, 50, 14782.
(b) Zhang, J.; Shao, Y.; Wang, H.-X.; Luo, Q.; Chen, J.-J.; Xu, D.-M.; Wan, X.-B. Org. Lett. 2014, 16, 3312.
(c) Mondal, B.; Sahoo, S. C. Pan, S. C. Eur. J. Org. Chem. 2015, 3135.
[14] (a) Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Science 2010, 328, 1376.
(b) Ma, L.-J.; Wang, X.-P.; Yu, W.; Han, B. Chem. Commun. 2011, 47, 11333.
(c) Yuan, Y.-C.; Hou, W.-J.; Zhang-Negrerie, D.; Zhao, K.; Du, Y.-F. Org. Lett. 2014, 16, 5410.
(d) Xu, W.; Nachtsheim, B. J. Org. Lett. 2015, 17, 1585.
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