陈玉,柏舜.3-烷基-7-甲基-5,6,7,8-四氢-3H-吡啶并[4',3': 4,5]噻吩并[2,3-d]嘧啶-4-酮衍生物的合成[J].中南民族大学学报自然科学版,2013,32(1):24-27
3-烷基-7-甲基-5,6,7,8-四氢-3H-吡啶并[4',3': 4,5]噻吩并[2,3-d]嘧啶-4-酮衍生物的合成
Synthesis of 3-Alkyl-7-methyl-5,6,7,8-tetrahydro-3H-pyrido[4',3 ': 4,5]thieno[2,3-d]pyrimidin-4-one Derivatives
  
DOI:10.12130/znmdzk.20130106
中文关键词: Gewald 反应  四氢吡啶并噻吩并嘧啶酮  乙氧基亚甲胺中间体
英文关键词: Gewald reaction  tetrahydropyridothienopyrimidinone  ethoxymethyleneamino intermediate
基金项目:国家科技支撑计划资助项目(2012BAI27B06)
作者单位
陈玉,柏舜 中南民族大学化学与材料科学学院武汉430074 
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中文摘要:
      通过Gewald 反应,在吗啡啉催化下,1-甲基-4-哌啶酮、氰乙酸乙酯与硫粉反应制得了中间体2-氨基-6-甲基-4,5,6,7-四氢噻吩并[2,3-c]吡啶-3-甲酸乙酯2,中间体2 与原甲酸三乙酯在醋酸酐催化下生成了乙氧基亚甲胺中间体3,最后再与相应的伯胺反应合成了3 个新的化合物: 3-烷基-7-甲基-5,6,7,8-四氢-3H-吡啶并[4',3 ': 4,5]噻吩并[2,3-d]嘧啶-4-酮衍生物( 4a~4c).产物结构经1HNMR,13CNMR,IR,MS 确证.结果表明: 该方法原料易得、条件温和、收率较高.
英文摘要:
      An intermediate,2-amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate 2 was synthesized by 1-methyl-4-piperidone,ethyl cyanoacetate and sulfur through Gewald reaction under the catalysis of morpholine. Then ethoxymethyleneamino intermediate 3 was synthesized by intermediate 2 and triethyl orthoformate under the catalysis of acetic anhydride.Then 3 unreported 3-alkyl-7-methyl-5,6,7,8-tetrahydro-3H-pyrido[4',3': 4,5]thieno[2,3-d]pyrimidin-4-one derivatives (4a~4c) were obtained from intermediate 3 reaction with the corresponding amines. Their structures were confirmed by 1H NMR,13CNMR,IR,MS. The result showed that this method is easily available with mild reaction conditions and high yield.
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