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5-甲基-6,7-二氢-5H-环戊并吡嗪的合成

Synthesis of 5-methyl-6,7-dihydro-5H-cyclopentapyrazine

  • 摘要: 为改进5-甲基-6,7-二氢-5H-环戊并吡嗪(化合物2)的合成工艺条件,以甲基环戊烯醇酮和乙二胺为原料,无水乙醇作溶剂,二氧化锰作氧化剂,经缩合和氧化反应合成了化合物2,优化了合成条件,并采用1H NMR和IR技术对产物结构进行了表征。结果表明:当无水乙醇用量20 mL、n(甲基环戊烯醇酮):n(乙二胺)=1:1.5(摩尔比)、60℃恒温反应2 h时,5-甲基-3,4,6,7-四氢-2H-环戊并吡嗪(化合物1)的收率达到95.7%;当n(氢氧化钾):n(二氧化锰):n(化合物1)=1:2.4:0.6、无水乙醇用量10 mL、80℃恒温反应15 h时,化合物2的收率为64.3%。

     

    Abstract: Cyclopenapyrazine compounds have important sensory properties in food and tobacco smoke.With anhydrous ethanol as solvent,manganese dioxide as oxidant,5-methyl-6,7-dihydro-5H-cyclopentapyrazine(Compound 2) was synthesized by methyl cyclopentenolone and ethylenediamine via condensation cyclization and oxidation.Moreover,the synthesis conditions were optimized,and the structures of the products were characterized by 1H NMR and IR.The results showed that the yield of 5-methyl-3,4,6,7-tetrahydro-2H-cyclopentapyrazine(Compound 1) was 95.7% under the optimized conditions of anhydrous ethanol 20 mL,n(methyl cyclopentenolone):n(ethylenediamine)=1:1.5,reacting for 2 hours at a constant temperature of 60℃.When n(potassium hydroxide):n(manganese dioxide):n(Compound 1)=1:2.4:0.6 and the amount of anhydrous ethanol was 10 mL,the yield of Compound 2 reached 64.3% after reacting for 15 hours at 80℃.

     

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