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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (01): 75-80. 上一篇    下一篇

研究论文

5-甲基-3-喹喔啉-2-基-4-乙氧羰基异噁唑及其衍生物的合成

王厚勇1,刘方明a b,阎琴1,郭群胜3   

  1. (a新疆大学化学化工学院 乌鲁木齐 830046)
    (b杭州师范学院化学系 杭州 310012)
    (c 南开大学元素有机化学研究所 天津 300071)
  • 收稿日期:2004-01-31 修回日期:2004-03-27 发布日期:2004-12-30
  • 通讯作者: 刘方明

Synthesis of Ethyl 5-Methyl-3-(quinoxalin-2-yl)-isoxazole-4 Carboxylate and Their Derivatives

WANG Hou-Yonga,LIU Fang-Ming1,2,YAN Qina,GUO Qun-Shengc   

  1. (a Department of Chemistry, Xinjiang Uniνersity, Urumqi 830046)
    (b Department of Chemistry, Hangzhou Teachers’ College, Hangzhou 310012)
    (c Institute of Elemento-Organic Chemistry, Nankai Uniνersity, Tianjin 300071)
  • Received:2004-01-31 Revised:2004-03-27 Published:2004-12-30
  • Contact: LIU, Fang-Ming

PDF

3229

被引次数

33

以α-氯代喹喔啉-2-甲醛肟(3)与乙酰乙酸乙酯的钠盐经1,3-偶极环加成制得关键中间体5-甲基-3-喹喔啉-2-基-4-乙氧羰基异噁唑(4). 以化合物4为原料在不同条件下, 合成了一系列新的1,3,4-噁二唑啉(7), 1,2,4-均三唑的Mannich碱衍生物10a～10f, 11a～11f, 12a～12f. 化合物的结构经元素分析, IR, 1H NMR和MS确认, 并对其波谱性质进行了讨论.

关键词: 4-均三唑, 1, Mannich碱, 2, 喹喔啉-2-甲醛, 4-噁二唑啉, 异噁唑, 3, 1

The key intermediate ethyl 5-methyl-3-(quinoxalin-2-yl)-isoxazole-4-carboxylate (4) was obtained by 1,3-dipolar cycloaddition reaction of 2-(1-hydroxylimino-1-chloro-methyl)-quinoxaline (3) with sodium 1-aceto-1-ethoxycarbonyl-methide, which was converted to hydrazide 5 by treating with hydrazine hydrate. Condensation of 5 with aromatic aldehydes gave corresponding hydrazones 6, then cyclization of 6 in Ac2O afforded 1,3,4-oxadiazolines 7a～7f. Thiosemicarbazides 8 prepared by treatment of the hydrazide 5 with suitable isothiocyanates, were cyclized in 1 mol•L－1 NaOH aqueous solution to give 5-thio-1,2,4- triazolines 9, and the Mannich base 10a～10f, 11a～11f and 12a～12f were synthesized. Their structures were analyzed and established by elemental analysis, IR, 1H NMR and MS spectra.

Key words: quinoxaline-2-carbaldehyde, 1, 1, 4-oxadiazoline, Schiff base, 3, 2, 4-triazole, isoxazole