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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1830-1835. 上一篇    下一篇

研究简报

N8-芳基取代4-氨基-6-氯-7(8H)-蝶啶酮的合成

段崇刚a,b ; 徐为人c ; 汤立达c ; 贾 炯a ; 王建武*,a   

  1. (a山东大学化学与化工学院 济南 250100)
    (b山东省医药工业研究所 济南 250100)
    (c天津药物研究院 天津 300193)
  • 收稿日期:2008-01-02 修回日期:2008-05-08 发布日期:2008-10-20
  • 通讯作者: 王建武

Synthesis of 8-Aryl-substituted 4-amino-6-chloro-8H-pteridin-7-one

DUAN, Chong-Gang a,b ; XU, Wei-Ren c; TANG, Li-Da c ; JIA, Jiong a ; WANG, Jian-Wu*,a
  

  1. (a College of Chemistry and Chemical Engineering, Shandong University, Jinan 250100) (b Shandong Institute of Pharmaceutical Industry, Jinan 250100)
    (c Tianjin Institute of Pharmaceutical Research, Tianjin 300193)
  • Received:2008-01-02 Revised:2008-05-08 Published:2008-10-20
  • Contact: WANG, Jian-Wu

PDF

1348

被引次数

5

通过N4-芳基取代4,5,6-三氨基嘧啶与草酸二水合物环合, 得到N8-芳基取代4-氨基-5,8二氢-6,7-蝶啶二酮, 再经氯代, 得到新型N8-芳基取代4-氨基-6-氯-7(8H)-蝶啶酮, 用红外光谱、核磁共振氢谱、核磁共振碳谱、质谱和元素分析确证了其结构. 用X-ray单晶衍射测定了4-氨基-6-氯-8-对甲苯基-7(8H)-蝶啶酮(3a)的晶体结构, 证明了环合反应的区域选择性.

关键词: 三氨基嘧啶, 合成, 草酸, 蝶啶酮, 环合

A series of novel 8-aryl substituted 4-amino-6-chloro-8H-pteridin-7-one derivatives were synthesized by cyclization of 4-[(un)substituted anilino]-5,6-diaminopyrimidine with oxalic acid dihydrate and subsequent chlorination. Their structures were confirmed by 1H NMR, 13C NMR, IR, ESI-MS and elemental analysis. The structure of 4-amino-6-chloro-8-p-tolyl-8H-pteridin-7-one (3a) was further determined by X-ray crystallographic analysis, providing a proof of the regioselectivity in the related cyclization reaction.

Key words: oxalic acid, triaminopyrimidine, cyclization, synthesis, pteridinone