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2-氯-3-烃基-5,6-二甲基吡嗪的合成及其烷氧基化和烷硫基化反应

Synthesis of 2-chloro-3-alkyl-5,6-dimethylpyrazine and its alkoxylation and alkylthiolation

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【作者】 孙德华蔡松传赵焘南张道信包燕雏

【Author】 Cai Songchuan Zhao Daonan Zhang Daoxin Bao Yanchu (Department of Chemistry,Nanjing University,Nanjing 210008)

【机构】 南京大学化学系南京大学化学系 南京210008南京210008

【摘要】 5-烃基-2,3-二甲基吡嗪-1-N-氧化物与三氯氧磷在回流温度下反应制得6种2-氯-3-烃基-5,6-二甲基吡嗪,产率71~82%。由2-氯-3-异丙基-5,6-二甲基吡嗪与烷醇钠反应得4种相应的烷氧基取代吡嗪,产率20.3~70.3%。由固-液相转移催化2-氯-3-异丙基(或苄基)-5,6-二甲基吡嗪与硫醇反应得4种相应的烷硫基取代吡嗪,产率47.5~68%。合成化合物的结构经元素分析和 IR、~1HNMR、MS 谱测定与预期结构相符。

【Abstract】 Reaction of 5-alkyl-2,3-dimethylpyra-zinc-1-N-oxides with phosphoryl chlorideunder reflux gave six 2-chloro-3-alkyl-5,6-dimethylpyrazines with good yields(71%~82%),among which five are new compounds.Alkoxylation of 2-chloro-3-isopropyl-5,6-dimethylpyrazine in R’ONa-R’OH underreflux gave four corresponding 2-alkoxy-3-isopropyl-5,6-dimethylpyrazines withyields of 20.3%~70.3%.Four 2-alkylthio-3-isopropyl (or benzyl)-5,6-dime thylpyrazineswere obtained from the alkylthiolation of 2-chloro-3-isopropyl(or benzyl)-5,6-dime-thylpyrazines with R~2SH under solid-liquidphase transfer catalytic conditions with satis-factory yields(47.5%~68%),all of which arenew compounds.Their structures were con-firmed by elemental analysis,IR,~1HNMR andMS spectrometry.

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