Twelve polyhedronylcarbonyl chloroethylureas were synthesized by the condensation of acylfluoride and chloroethylurea in the ionic liquid [bmim][BF4] with the polyhedron dicarboxylic acids as starting materials. The structures have been characterized by 1H NMR, 13C NMR and MS techniques. Comparison with the traditional methods of acylchloride as intermediate, this procedure has the advantages of better yield, simplified operation and environmental benignity.
ZHANG Hong-Lei
,
ZHU Xiao-He
,
YAN Hong
,
SONG Xiu-Qing
. Synthesis of Polyhedronylcarbonyl Chloroethylureas Using Acylfluoride in Ionic Liquid[J]. Chinese Journal of Organic Chemistry, 2012
, 32(02)
: 344
-348
.
DOI: 10.6023/cjoc1107222
[1] Stewart, B. W.; Kleihues, P. IARC Press 2003, 48.
[2] Loppky, H. N. ACS Symp. Ser. 1994, 553, 1.
[3] Hilgeroth, A.; Baumeister, U. Chem. Eur. J. 2001, 7, 4599.
[4] Carell, T.; Winter, E. A.; Bashirhashemi, A.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 2059.
[5] Bashirhashemi, A.; Li. J. C. J. Org. Chem. 1995, 60, 698.
[6] Qin, Y.; Deng, H. F.; Yan, H.; Zhong, R. G. J. Mol. Graph. Model 2011, 29, 826.
[7] Mahkam, M. Macromol. Symp. 2003, 200, 209.
[8] Galow, T. H.; Rodrigo, J.; Cleary, K. J. Org. Chem. 1999, 64, 3745.
[9] Lou, W. Y.; Zong, M. H.; Wu, H. Green Chem. 2005, 7, 500.
[10] Shi, D. Q.; Ni, S. N.; Yang, F. J. Heterocycl. Chem. 2008, 45, 1275.
[11] Madeira Lau, R.; van Rantwijk, F.; Seddon, K. R. Org. Lett. 2000, 2, 4189.
[12] Imrie, C.; Elago, E. R. T.; Williams, N.; McCleland, C. W.; Engelbrecht, P. J. Organomet. Chem. 2005, 690, 4959.
[13] Ying, A.-G.; Ye, W.-D.; Liu, L.; Wu, G.-F.; Chen, X.-Z.; Qian, S.; Zhang, Q.-P. Chin. J. Org. Chem. 2008, 28, 2081 (in Chinese). (应安国, 叶伟东, 刘泺, 吴国锋, 陈新志, 钱胜, 张秋萍, 有机 化学, 2008, 28, 2081.)
[14] Chen, W.-Y.; Lu, Y.; Zhang, Y. Chin. J. Org. Chem. 2006, 26, 87 (in Chinese). (陈维一, 陆军, 张勇, 有机化学, 2006, 26, 87.)
[15] Bliese, M.; Tsanaktsidis, J. Aust. J. Chem. 1997, 50, 189.
[16] Guan, X. P.; Su, Z.; Du, J. W. J. Energ. Mater. 1997, 15, 139.
[17] Harman, D. G.; Blanksby, S. J. Org. Biomol. Chem. 2007, 5, 3495.
[18] Luh, T. Y.; Stock, L. M.; J. Org. Chem. 1979, 37, 338.
[19] Chapman, N. B.; Key, J. M.; Toyne, K. J. J. Org. Chem. 1970, 35, 3860.
[20] Groß, S.; Laabs, S.; Scherrmann, A.; Sudau, A.; Zhang, N.; Nubbemeyer, U. J. Prakt. Chem. 2000, 342, 711.