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Synthesis of 1,4,5-Triarylpyrazoles from the Addition Products of α,β-Chalcones with New Ion-Supported [Hydrox-yl(tosyloxy)iodo]benzenes
Received date: 2014-10-15
Revised date: 2014-12-05
Online 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.
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]. Chinese Journal of Organic Chemistry, 2015 , 35(5) : 1137 -1145 . DOI: 10.6023/cjoc201410022
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