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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (8): 893-897. 上一篇    下一篇

研究论文

新型1,2,4-三唑并[3,2-d][1,5]苯并氧氮杂䓬-2-酮的合成

李诤, 王全瑞, 陶凤岗*   

  1. 复旦大学化学系 上海 200433
  • 收稿日期:2003-10-28 修回日期:2003-01-09 接受日期:2004-02-16 发布日期:2022-09-20
  • 通讯作者: * E-mail: fgtao@fudan.edu.cn
  • 基金资助:
    国家自然科学基金(No. 20372015)资助项目.

Synthesis of Novel 1,2,4-Triazolo[3,2-d][1,5]benzoxazepin-2-ones

LI Zheng, WANG Quan-Rui, TAO Feng-Gang*   

  1. Department of Chemistry, Fudan University, Shanghai 200433
  • Received:2003-10-28 Revised:2003-01-09 Accepted:2004-02-16 Published:2022-09-20

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取代苯并二氢吡喃-4-酮(1)的芳腙在冰醋酸中与KNCO发生[3+2]环加成反应,加成产物经KMnO4氧化开环得偕偶氮异氰酸酯(3). 3在HBF4的催化下发生环化-重排反应,合成得到一系列新型6-7-5三环系1,2,4-三唑并[3,2-d][1,5]苯并氧氮杂䓬2-酮(5a～5g).由X单晶衍射测定了化合物5a的晶体结构.

关键词: 偕偶氮异氰酸酯, 关环, 重排, 1,2,4-三唑并[3,2-d][1,5]苯并氧氮杂䓬-2-酮

A series of novel tricyclic O,N-heterocycles 5a～5g, a kind of unprecedented 1,2,4-triazolo[3,2-d]~[1,5]benzoxazepin-2-ones, have been achieved via acid-induced ringclosure of isocyanatoarylazo compounds 3, which were preparedfrom chroman-4-one in three steps, followed by feasible rearrangement. The structural assignment of 5a has been ultimately accomplished by X-ray diffraction analysis.

Key words: geminal arylazo isocyanate, ring closure, rearrangement, 1,2,4-triazolo[3,2-d][1,5]benzoxazepin-2-one