Chinese Journal of Organic Chemistry >
One-Pot Three-Component Synthesis of Novel Carbamate Compounds Mediated by Zinc Powder
Received date: 2014-02-28
Revised date: 2014-04-28
Online published: 2014-05-05
Supported by
Project supported by the National Natural Science Foundation of China (No. U1204204) and the Youth Foundation of Shangqiu Normal University (No. 2011QN17).
A series of novel carbamate compounds were obtained from one pot three component reaction of aldehydes, bromohydrocarbons and isocyanates mediated by zinc powder under room temperature. This protocol has advantages of mild conditions, simple work-up, high yield, easily available starting materials and fast reaction rate. The structures of all products were characterized by 1H NMR, 13C NMR, IR, HRMS and elemental analysis.
Key words： carbamate compounds; zinc powder; one-pot; three-component; synthesis
Meng Tuanjie , Liu Lantao , Ren Lifeng , Liu Xinming , Wang Xiaojuan , Zhao Wenxian . One-Pot Three-Component Synthesis of Novel Carbamate Compounds Mediated by Zinc Powder[J]. Chinese Journal of Organic Chemistry, 2014 , 34(8) : 1588 -1594 . DOI: 10.6023/cjoc201402040
[1] (a) Adams, P.; Baron, F. A. Chem. Rev. 1965, 65, 567.
(b) Tai-The, W.; Huang, J.; Arrington, N. D.; Dill, G. M. J. Agric. Food Chem. 1987, 35, 817.
(c) Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett. 2000, 41, 6347.
(d) Pandey, R. K.; Dagade, S. P.; Dongare, M. K.; Kumar, P. Synth. Commun. 2003, 33, 4019.
[2] (a) Qiang, X.; Yuan, W.; Sang, Z.; Deng, Y. Chin. J. Org. Chem. 2013, 33, 621 (in Chinese).
(强晓明, 袁文, 桑志培, 邓勇, 有机化学, 2013, 33, 621.)
(b) Niphakis, M. J.; Johnson, D. S.; Ballard, T. E.; Stiff, C.; Cravatt, B. F. ACS Chem. Neurosci. 2012, 3, 418.
(c) Fu, L.; Liu, X.; Ling, C.; Cheng, J.; Guo, X.; He, H.; Ding, S.; Yang, Y. Bioorg. Med. Chem. Lett. 2012, 22, 814.
(d) Sharma, V. K.; Lee, K-C.; Venkateswararao, E.; Joo, C.; Kim, M.-S.; Sharma, N.; Jung, S. H. Bioorg. Med. Chem. Lett. 2011, 21, 6829.
(e) Kumar, K.; Awasthi, D.; Lee, S-Y.; Zanardi, I.; Ruzsicska, B.; Knudson, S.; Tonge, P. J.; Slayden, R. A.; Ojima, I. J. Med. Chem. 2011, 54, 374.
(f) Hen, N.; Bialer, M.; Yagen, B. J. Med. Chem. 2012, 55, 2835.
[3] (a) Oertel, G. Polyurethane Handbook, Carl Hanser, Munich, 1985, p. 31.
(b) Babad, H.; Zeiler, A. G. Chem. Rev. 1973, 73, 75.
[4] Yadav, J. S.; Reddy, G. S.; Reddy, M. M.; Meshram, H. M. Tetrahedron Lett. 1998, 39, 3259.
[5] (a) Kumar, S.; Jain, S. New J. Chem. 2013, 37, 2935.
(b) Kumar, S.; Jain, S. Dalton Trans. 2013, 39, 15214.
(c) Guo, X.; Shang, J.; Li, J.; Wang, L.; Ma, Y.; Shi, F.; Deng, Y. Synth. Commun. 2011, 41, 1102.
(d) Angeles, E.; Santillan, A.; Martinez, I.; Ram_rez, A., Moreno, E.; Salmon, M.; Martinez, R. Synth. Commun. 1994, 24, 2441.
[6] (a) Kocak, A.; Ahmetli, G.; Kocak, N.; Malkondu, S.; Yaylaci, A.; Kurbanli, S. Synth. Commun. 2011, 41, 1629.
(b) Kocovsky, P. Tetrahedron Lett. 1986, 27, 5521.
[7] (a) Soldi, L.; Massera, C.; Costa, M.; Ca, N. D. Tetrahedron Lett. 2014, 55, 1379.
(b) Shang, J.; Liu, S.; Ma, X.; Lu, L.; Deng, Y. Green Chem. 2012, 14, 2899.
(c) Honda, M.; Sonehara, S.; Yasuda, H.; Nakagawa, Y.; Tomishige, K. Green Chem. 2011, 13, 3406.
(d) Kong, D.-L.; He, L.-N.; Wang, J.-Q. Synth. Commun. 2011, 41, 3298.
(e) Qi, C.; Huang, L.; Jiang, H. Synthesis 2010, 1433.
(f) Kayaki, Y.; Suzuki, T.; Ikariya, T. Chem. Asian J. 2008, 3, 1865.
(g) Ion, A.; Doorslaer, V. C.; Parvulescu, V.; Jacobs, P.; Vos, D. D. Green Chem. 2008, 10, 111.
(h) Li L.-Q.; Wang, X.-G.; Guo, S.-X.; Liu, C.-Y.; He, Y.-B. Chin. J. Org. Chem. 2007, 27, 519 (in Chinese).
(李立清, 王晓刚, 郭三霞, 刘重洋, 何益波, 有机化学, 2007, 27, 519.)
[8] (a) Guan, Z.-H.; Lei H.; Chen, M.; Ren, Z.-H.; Bai, Y.; Wang, Y.-Y. Adv. Synth. Catal. 2012, 354, 489.
(b) Zheng, S.; Li, F.; Liu, J.; Xia, C. Tetrahedron Lett. 2007, 48, 5883.
[9] (a) Kreye, O.; Wald, S.; Meier, M. A. R. Adv. Synth. Catal. 2013, 355, 81.
(b) Yoganathan, S.; Miller, S. J. Org. Lett. 2013, 15, 602.
(c) Hamon, F.; Prié, G.; Lecornué, F.; Papot, S. Tetrahedron Lett. 2009, 50, 6800.
[10] (a) Yoshimura, A.; Luedtke, M. W.; Zhdankin, V. V. J. Org. Chem. 2012, 77, 2087.
(b) Borah, A. J.; Phukan, P. Tetrahedron Lett. 2012, 53, 3035.
(c) Hiegel, G. A.; Hogenauer, T. J. Synth. Commun. 2005, 35, 2091.
[11] (a) Augustine, J. K.; Bombrun, A.; Mandal, A. B.; Alagarsamy, P.; Atta, R. N. Synthesis 2011, 1477.
(b) Lebel, H.; Leogane, O. Org. Lett. 2006, 8, 5717.
[12] (a) Yang, X.; Zhang, Y.; Ma, D. Adv. Synth. Catal. 2012, 354, 2443.
(b) Kianmehr, E.; Baghersad, M. H. Adv. Synth. Catal. 2011, 353, 2599.
[13] Vinogradova, E. V.; Park, N. H.; Fors, B. P.; Buchwald, S. L. Org. Lett. 2013, 15, 1394.
/
| 〈 |
|
〉 |
