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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (11): 1454-1457. 上一篇    下一篇

研究简报

2-氨基-3-氰基-4-芳基-6-甲氧基-1,4,9,10-四氢萘并[2,1-b]吡喃衍生物的一步合成

王香善*,a,b,c, 史达清a,c, 魏贤勇b, 宗志敏b   

  1. a徐州师范大学化学系 徐州 221116;
    b中国矿业大学化学工程学院 徐州 221008;
    c江苏省药用植物生物技术重点实验室 徐州 221116
  • 收稿日期:2004-01-13 修回日期:2004-05-28 接受日期:2004-05-28 发布日期:2022-09-21
  • 通讯作者: * E-mail: xswang1974@yahoo.com or xswang@xznu.edu.cn
  • 基金资助:
    江苏省青蓝工程基金(No. QL98001)和江苏省教育厅高校自然科学基金(No. 02KJB150139)资助项目.

One-Step Synthesis of 2-Amino-3-cyano-4-aryl-6-methoxy-1,4,9,10- tetrahydronaphtho[2,1-b]pyran Derivatives

WANG Xiang-Shan*,a,b,c, SHI Da-Qinga,c, WEI Xian-Yongb, ZONG Zhi-Minb   

  1. aDepartment of Chemistry, Xuzhou Normal University, Xuzhou 221116;
    bSchool of Chemical Engineering, China University of Mining and Technology, Xuzhou 221008;
    cThe Key Laboratory of Biotechnology on Medical Plant, Xuzhou 221116
  • Received:2004-01-13 Revised:2004-05-28 Accepted:2004-05-28 Published:2022-09-21

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以芳醛、丙二腈和7-甲氧基-1,2,3,4-四氢萘-2-酮为原料,在六氢吡啶催化下以乙醇为溶剂,在室温合成了一系列新的2-氨基-3-氰基-4-芳基-6-甲氧基-1,4,9,10-四氢萘并[2,1-b]吡喃衍生物,反应条件温和,产率较高,并通过IR, 1H NMR和元素分析表征产物的结构,还通过单晶X射线衍射分析确证产物的构象.

关键词: 7-甲氧基-2-萘酮, 六氢吡啶, 萘并[1,2-b]吡喃, 合成

Using piperidine as catalyst and ethanol as solvent, a seriesof new 2-amino-3-cyano-4-aryl-6-methoxy-1,4,9,10-tetrahydronaphtho[2,1-b]pyran derivatives were synthesized by one-pot reaction of aromatic aldehydes, malononitrile and 7-methoxy-1,2,3,4-tetrahydronaphthalen-2-one atroom temperature in good yields. The reaction conditions were mild. The structures of the products were characterized by IR, 1H NMR spectra and elementalanalysis. The conformation of compound 4a was also confirmed by X-ray analysis.

Key words: 7-methoxylnaphthalen-2-one, piperidine, naphtho[2,1-b]pyran, synthesis