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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (12): 2102-2105. 上一篇    下一篇

研究论文

桥连的双[噻吩并[2,3-d]嘧啶-4(3H)-酮]的合成

方正东, 吕鉴泉   

  1. (湖北师范学院化学与环境工程学院 黄石 435002)
  • 收稿日期:2011-04-09 修回日期:2011-06-23 发布日期:2011-08-29
  • 通讯作者: 方正东 E-mail:zdfangluo@sina.com

Synthesis of Bridged Bis(thieno[2,3-d]pyrimidin-4(3H)-ones)

Fang Zheng-Dong ,LU JIAN-QUAN   

  1. (College of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002)
  • Received:2011-04-09 Revised:2011-06-23 Published:2011-08-29
  • Contact: Fang Zheng-Dong E-mail:zdfangluo@sina.com

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2-氨基-4-三氟甲基-5-甲基-噻吩-3-羧酸乙酯(1)与三苯基膦、六氯乙烷及三乙胺反应, 以84%的产率得到膦亚胺2. 在碳酸钾的催化下, 膦亚胺2与芳基异氰酸酯和双官能亲核试剂的串联氮杂Wittig 反应制得新型桥连的双[噻吩并[2,3-d]嘧啶-4(3H)-酮] 3, 产率为58%～82%. 所有产物结构经IR, 1H NMR, MS表征和元素分析确证.

关键词: 桥连, 噻吩并[2,3-d]嘧啶-4(3H)-酮, 氮杂Wittig反应, 膦亚胺

Ethyl 2-amino-4-trifluoromethyl-5-methyl-thiophene-3-carboxylate (1) reacted with triphenylphosphine in hexachloroethane and triethylamine to give iminophosphorane 2 in 84% yield. Further aza-Wittig reactions of iminophosphorane 2 with aromatic isocyanate and bi-functional nucleophilic reagents produced novel bridged bis(thieno[2,3-d]pyrimidin-4(3H)-ones) 3 in the presence of catalytic amounts of potassium carbonate in 58%～82% yields. The structures of all products were confirmed by IR, 1H NMR, MS techniques and elemental analysis.

Key words: bridged, thieno[2,3-d]pyrimidin-4(3H)-one, aza-Wittig reaction, iminophosphorane