Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1137-1145.DOI: 10.6023/cjoc201410022 Previous Articles     Next Articles



郑纯智a, 徐小丹b, 王雅珍a, 赵德建a, 张继振a   

  1. a 江苏理工学院化学与环境工程学院 常州 213001;
    b 常州大学石油化工学院 常州 213164
  • 收稿日期:2014-10-15 修回日期:2014-12-05 发布日期:2015-01-13
  • 通讯作者: 张继振

Synthesis of 1,4,5-Triarylpyrazoles from the Addition Products of α,β-Chalcones with New Ion-Supported [Hydrox-yl(tosyloxy)iodo]benzenes

Zheng Chunzhia, Xu Xiaodanb, Wang Yazhena, Zhao Dejiana, Zhang Jizhena   

  1. a School of Chemistry and Environmental Engineering, Jiangsu Technology of University, Changzhou 213001;
    b School of Petrochemical Engineering, Changzhou University, Changzhou 213164
  • Received:2014-10-15 Revised:2014-12-05 Published:2015-01-13

Three new N-(4-iodophenyl)pyridinium salts 7~9 were synthesized from pyridine and 1-chloro-2,4-dinitrobenzene by three steps. In these steps, N-(2,4-dinitrophenyl)pyridinium chloride 5 was prepared through the nucleophilic substitution reaction at first. Then N-(4-iodophenyl)pyridinium chloride was obtained from 4-iodoaniline and 5 through the Zincke's reaction. At last the salts 7~9 were got in aqueous solution by anion exchange. And then three new pyridinium salts supported [4-hydroxy(tosyloxy)iodo]benzene conjugated reagents [N-(4-hydroxyl(tosyloxy)iodophenyl)pyridinium p-toluenesulfonate 10, N-(4-hydroxyl(tosyloxy)iodophenyl)pyridinium tetrafluoroborate 11 and N-(4-hydroxyl(tosyloxy)iodophenyl)pyridinium hexafluorostibnate 12] were prepared from the salts 7~9 and p-toluenesulfonic acid with m-chlorobenzo- peroxoic as oxidizer. These reagents were solid at room temperature and had not the moisture absorption property. The adducts of α,β-chalcones, 1,3-diaryl-2,3-di(tosyloxy)-1-acetone 14 (two of them were new compounds), were prepared using the reagents 10, 11 and N-[4-hydroxyl(tosyloxy)iodobenzyl]pyridinium tetrafluoroborate 4 respectively. The yields of compounds 14 from reagents 10, 11 were also found to be higher than that from reagent 4. Finally, 1-phenyl-4,5-diarylpyrazoles (two of them were new com-pounds) were prepared from 14 and phenylhydrazine by cyclization reaction. After the addition reaction, the reagents were transformed into the corresponding ion-supported iodobenzenes, which could be easily recovered and regenerated with no lost of the addition reaction activity.

Key words: task-specific ionic liquid, [hydroxy(tosyloxy)iodo]benzene, pyridine, 1-phenyl-4,5-diarylpyrazoles, chalcone, synthesis