Chinese Journal of Organic Chemistry >
Microwave-Assisted Synthesis of Novel Molecular Tweezers Based on Deoxycholic Acid with Arm of Substituted Thiosemicarbazides
Received date: 2012-08-27
Revised date: 2012-09-27
Online published: 2012-10-09
Supported by
Project supported by the Fundamental Research Funds of Central Universities, Southwest University for Nationalities (Nos. 12ZYXS77, 11NZYTH05), the Science and Technology Department of Sichuan Province (No. 2012SZ0160) and the National Foreign Expert Bureau (No. 2012-29).
Ten new molecular tweezers based on deoxycholic acid were synthesized in good yields by using deoxycholic acid methyl ester as spacer to bridge different substituted thiosemicarbazides via triphosgene under microwave irradiation. Their structures were charactetized by 1H NMR, IR, MS techniques and elemental analysis. The microwave method has distinct advantages such as short reaction time, high yields and eco-friendly to the environment. The recognition properties of these molecular tweezers for Cl-, Br-, I-, NO3- anions were investigated by UV-vis spectra titration. The result indicated that this type of molecular tweezers has good binding properties for anions.
Xia Zhenyang , Zhao Zhigang , Shi Zhichuan , Liu Min . Microwave-Assisted Synthesis of Novel Molecular Tweezers Based on Deoxycholic Acid with Arm of Substituted Thiosemicarbazides[J]. Chinese Journal of Organic Chemistry, 2013 , 33(01) : 132 -137 . DOI: 10.6023/cjoc201208031
[1] Martinez, M. R.; Sancenon, F. Chem. Rev. 2003, 103, 4419.
[2] Gong, W. T.; Bao, S.; Wang, F. R.; Ye, J. W.; Ning, G. L.; Hiratani, K. Tetrahedron Lett. 2011, 52, 630.
[3] Chahar, M.; Pandey, P. S. Tetrahedron 2008, 64, 6488.
[4] Kondo, S. I.; Nagamine, M.; Karasawa, S. Ishihara, M.; Unno, M.; Yano, Y. Tetrahedron 2011, 67, 943.
[5] Ghosh, K.; Kar, D.; Chowdhury, P. R. Tetrahedron Lett. 2011, 52, 5098.
[6] Chhatra, R. K.; Kumar, A.; Pandey, P. S. J. Org. Chem. 2011, 76, 9086.
[7] Xue, W. J.; Li, L.; Li, Q.; Wu, A. X. Talanta 2012, 88, 734.
[8] Zhao, Z. G.; Liu, X. L.; Li, Q. H.; Chen, S. H. Chin. J. Org. Chem. 2009, 29, 1336 (in Chinese). (赵志刚, 刘兴利, 李清寒, 陈淑华, 有机化学, 2009, 29, 1336.)
[9] Lerouge, M. H.; Hudhomme, P.; Salle, M. Chem. Soc. Rev. 2011, 40, 30.
[10] Leblond, J.; Petitjean, A. ChemPhysChem 2011, 12, 1043.
[11] Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629.
[12] Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
[13] 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.)
[14] Qiu, L. Y.; Shi, Z. C.; Mei, Q. G.; Zhao, Z. G. J. Chem. Res. 2011, 35, 456.
[15] Zhao, Z. G.; Liu, X. L; Li, H.; Tang, X. L. Chin. J. Org. Chem. 2008, 28, 1233 (in Chinese). (赵志刚, 刘兴利, 李晖, 唐晓丽, 有机化学, 2008, 28, 1233.)
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