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
收稿日期: 2014-10-15
修回日期: 2014-12-05
网络出版日期: 2015-01-13
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
以吡啶和2,4-二硝基氯苯为起始原料, 经过三步反应, 合成了三种N-(4-碘苯基)吡啶盐新化合物7~9, 然后在间氯过氧苯甲酸氧化下, 7~9分别与对甲苯磺酸反应制备了三种新的吡啶盐负载羟基(对甲苯磺酰氧基)碘苯共轭试剂: N-[4-羟基(对甲苯磺酰氧基)碘苯基]吡啶对甲苯磺酸盐10、四氟硼酸盐11和六氟锑酸盐12. 三种新试剂室温下都是固体, 在空气中没有吸湿性. 分别研究了试剂10、11和N-[4-羟基(对甲苯磺酰氧基)碘苯甲基]吡啶四氟硼酸盐4对α,β-查尔酮及其衍生物的加成反应, 成功地合成了1,3-二芳基-2,3-二对甲苯磺酰氧基-1-丙酮14(其中二个是新化合物), 共轭试剂10、11和α,β-查尔酮及其衍生物的加成产率比非共轭试剂4高. 然后14和苯肼发生环合反应制备了1-苯基-4,5-二芳基吡唑(其中二个是新化合物). 回收后的离子负载碘苯容易再生成试剂, 而再生试剂和查尔酮及其衍生物的加成反应活性几乎保持不变.
关键词： 功能性离子液体; 羟基(对甲苯磺酰氧基)碘苯; 吡啶; 1-苯基-4,5-二芳基吡唑; 查尔酮; 合成
郑纯智 , 徐小丹 , 王雅珍 , 赵德建 , 张继振 . 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[J]. 有机化学, 2015 , 35(5) : 1137 -1145 . DOI: 10.6023/cjoc201410022
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.
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