Chinese Journal of Organic Chemistry >
Efficient One-Pot Synthesis of 3,3-Dimethyl-diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5-dione-9-thione Derivatives
Received date: 2015-10-10
Revised date: 2015-12-03
Online published: 2016-01-21
Supported by
Project supported by the National Science and Technology Project (No. 2001BA323C) and the Graduate Innovation Foundation of Jiangxi Province (No. YC2015-B023).
Six kinds of 3,3-dimethyl-diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]-undecane-1,5-dione-9-thione derivatives were sythesized by the three component one-pot reaction of aromatic aldehydes with thiourea and 2,2-dimethyl-1,3-dio-xane-4,6-dione in the presence of molecular iodine under solvent-free conditions. The results indicated that the yields ranged from 73% to 91% at 80 ℃ for 3.0~6.0 h using 10 mol% iodine (relative to the substrate of 2,2-dimethyl-1,3-dioxane-4,6-dione). Furthermore, the present procedure with high yields was milder conditions and simpler post-treatment process.
Xu Zhaohui , Zhou Peng , Liu Deyong . Efficient One-Pot Synthesis of 3,3-Dimethyl-diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5-dione-9-thione Derivatives[J]. Chinese Journal of Organic Chemistry, 2016 , 36(5) : 1099 -1103 . DOI: 10.6023/cjoc201510009
[1] Rovnyak, G. C.; Kimball, S. D.; Barbara, B.; Gabriella, C.; John, D. D.; Jack, G.; Anders, H.; Mary, M.; James, P. M. J. Med. Chem. 1995, 38, 19.
[2] Snider, B. B.; Shi, Z. J. Org. Chem. 1993, 58, 3828.
[3] Arimoto, H.; Hayakawa, I.; Kuramoto, M.; Uemure, D. Tetrahedron Lett. 1998, 39, 861.
[4] Chou, T.; Kuramoto, M.; Otani, Y.; Shkano, M.; Yazawa, K.; Uemere, D. Tetrahedron Lett. 1996, 37, 3867.
[5] Dipak, P.; Debajyoti, B.; Mukut, G.; Hu, W. H. Mol. Diversity 2011, 15, 257.
[6] Srinivasa, R. J.; Divya, V.; Shubha, J. J. Chem. Pharm. Res. 2012, 4, 2373.
[7] Zhu, Y. L.; Huang, S. L.; Pan, Y. J. Eur. J. Org. Chem. 2005, 2354.
[8] Srinivasa, R. J.; Divya,V.; Shubha, J. J. Catal. 2013, 2013, 1.
[9] Xu, Z. H.; Tu, Y. H. Chin. J. Org. Chem.2015, 35, 1357 (in Chinese).
(许招会, 涂缘鸿, 有机化学, 2015, 35, 1357.)
[10] Naser, M.; Khalil, P.; Masoud, B.; Soudabeh, K. Asian J. Chem. 2013, 25, 3373.
[11] Li, J. J.; Sun, J.; Su, W. K. Lett. Org. Chem. 2010, 7,14.
[12] Dhevalapally, B. R.; Carlos, F. B. Chem. Eur. J.2004, 10,5323.
[13] Dohi, T.; Kita, Y. Chem. Commun. 2009, 28, 2073.
[14] Xu, W. J.; Zhang, W. S.; Yan, J. L. Chin. J. Appl. Chem. 2011, 28, 1143 (in Chinese).
(许文静, 张文龙, 闫金龙, 应用化学, 2011, 28, 1143.)
[15] Wang, D. L.; Dong, Z.; Liu, Z.; Yang, F. F. Chin. J. Org. Chem.2014, 34, 783 (in Chinese).
(王道林, 董哲, 刘忠, 杨菲菲, 有机化学, 2014, 34, 783.)
[16] Yan, N.; Xu, Z. H.; Liu, B. Chin. J. Spec. Petrochem. 2010, 27, 45 (in Chinese).
(严楠, 许招会, 刘百强, 精细石油化工, 2010, 27, 45.)
[17] Xu, Z. H.; Lin, C. H.; Liao, W. L. Chin. J. Appl. Chem. 2015, 32, 278 (in Chinese).
(许招会, 林春花, 廖维林, 应用化学, 2015, 32, 278.)
[18] Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959.
[19] Ahmad, S.; Ayoob, B.; Hamid, R. B. Mol. Diversity 2004, 8, 141.
[20] Yan. N.; Xiong, B.; Liao, W. L.; Xu, Z. H. Chin. J. Org. Chem.2010, 30, 1391 (in Chinese).
(严楠, 熊斌, 廖维林, 许招会, 有机化学, 2010, 30, 1391.)
/
| 〈 |
|
〉 |
