Methyl Carbonium Ion Migration during the Reaction of 4-Chloro-5-methoxyl-3(2H)-pyridazinone with Trifluoroethylation Agents

被引：3

作者：

Li, Qin ^{[1
]}

Lin, Guichun ^{[1
]}

Liu, Li ^{[1
]}

Yang, Zhenjun ^{[1
]}

Zhang, Li-He ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

MOLECULES | 2009年 / 14卷 / 02期

关键词：

4,5-Dichloro-3(2H)-pyridazinone; 4-Chloro-5-methoxy-3(2H)-pyridazinone; beta-Trifluoroethylation; Oxonium; Methyl group migration; Alkylation; ANTIARRHYTHMICS;

D O I：

10.3390/molecules14020777

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

To synthesize 4-chloro-5-methoxy-2-(beta-trifluoroethyl)-3(2H)-pyridazinone (4), the reactions of 4-chloro-5-methoxy-3(2H)-pyridazinone (5) with RCH2CF3 (R = I, TsO, MsO, TfO) in different solvents were studied. It was found that methyl group migration took place during this reaction. An oxonium salt 9 was suggested as the active intermediate for the formation of the byproduct 4-chloro-5-methoxy-2- methyl-3(2H)-pyridazinone (7) and 4-chloro-2-methyl-5-(beta-trifluoroethoxy)-3(2)-pyridazinone (8).

引用

页码：777 / 784

页数：8

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