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

doi:10.6023/cjoc201410022

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

Notes

新型离子负载羟基(对甲苯磺酰氧基)碘苯对α,β-查尔酮及其衍生物的加成产物用于1,4,5-三芳基吡唑的合成

郑纯智^a, 徐小丹^b, 王雅珍^a, 赵德建^a, 张继振^a

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 E-mail:zhangjizhen_9@aliyun.com

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

Zheng Chunzhi^a, Xu Xiaodan^b, Wang Yazhen^a, Zhao Dejian^a, Zhang Jizhen^a

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

1. Synthesis of 1,4,5-Triarylpyrazoles from the Addition Products of α,β-Chalcones with New Ion-Supported [Hydrox-yl(tosyloxy)iodo]benzenes.PDF(5276KB)

Abstract

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

Cite this article

Zheng Chunzhi, Xu Xiaodan, Wang Yazhen, Zhao Dejian, Zhang Jizhen. Synthesis of 1,4,5-Triarylpyrazoles from the Addition Products of α,β-Chalcones with New Ion-Supported [Hydrox-yl(tosyloxy)iodo]benzenes[J]. Chin. J. Org. Chem., 2015, 35(5): 1137-1145.

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新型离子负载羟基(对甲苯磺酰氧基)碘苯对α,β-查尔酮及其衍生物的加成产物用于1,4,5-三芳基吡唑的合成

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

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