摘要
以2,3-二氯-5-三氟甲基吡啶为原料,在氨水作用下,胺解生成2-氨基-3-氯-5-三氟甲基吡啶;然后与溴代丙酸乙酯环化,氢氧化钠水解生成8-氯-6-(三氟甲基)-咪唑[1,2a]吡啶-2-甲酸;最后,在氯化亚砜的作用下,8-氯-6-(三氟甲基)-咪唑[1,2a]吡啶-2-甲酸与2-氯-5-甲氧基苯磺酰胺反应得到目的产物三氟咪啶酰胺。经1H NMR光谱鉴定,产物与三氟咪啶酰胺结构一致。
2-amino-3-chloro-5-trifluoromethylpyridine was prepared by the reaction of 2,3-dichloro-5-trifluoromethylpyridine with aqueous ammonia. Then it was cyclized with ethyl bromopropionate in solution of ethanol,and hydrolyzed in the present of sodium hydroxide to give 8-chloro-6-(trifluoromethyl)-imidazo[1,2 a]pyridine-2-carboxylic acid. Finally,under the action of thionyl chloride, 8-chloro-6-(trifluoromethyl)-imidazole [1,2 a]pyridine-2-carboxylic acid was reacted with 2-chloro-5-methoxybenzenesulfonamide to give the target of fluazaindolizine. Identified by 1 H NMR spectrum, the product is consistent with the fluazaindolizine structure.
引文
[1]SAKAMOTO,EMIKO.Method for controlling harmful organisms by mixing specified granular formulation into soil:WO,2016013505[P].2016-01-28.
[2]BRAHM,LUTZ,LIEBMANN,BURGHARD,WILHELM,RONALD,et al.Pesticidal mixtures of biocontrol agent with at least one fungicidal,insecticidal or plant growth regulator:WO,2014079773[P].2014-05-30.
[3]LAHM G P.,DESAEGER J,SMITH B K.,et al.The discovery of fluazaindolizine:a new product for the control of plant parasitic nematodes[J].Bioorganic&Medicinal Chemistry Letters,2017,27(7):1572-1575.
[4]LAHM G P.,LETT R M,SMITH B T,et al.Preparation of sulfonamides as nematocides useful for controlling parasitic nematodes:WO,2010129500[P].2010-11-11.
[5]孙鹤,胡玮,王纵横,等.两个埃博霉素生物合成中间体修饰化合物的合成[J].有机化学,2008,28(4):657-662.
[6]HAGA T,FUJIKAWA K,KOYANAGI T,et al.Some new 2-substituted5-trifluoromethyl pyridines[J].Heterocycles,1984,22(1):117-124.
[7]MOHAN R,NUSS J,HARRIS J.Heterocyclic compounds and prodrugs as S1P receptor modulators for the treatment of disease:WO,2018211324[P].2018-10-22.
[8]MOHAN,R.Preparation of imidazopyridinyl oxodiazolyl pyrrolidinones for the treatment of diseases:WO,2017083756[P].2017-5-18.
