高等学校化学学报

高等学校化学学报

• 研究论文 • 上一篇    下一篇

由N-苯基[1,3]苯并噁嗪正离子与烯烃[4+2]反应合成喹啉并[1,2-c][1,3]苯并噁嗪-6-酮衍生物

王俊蒲, 张炜, 黄利敏   

  1. 兰州大学功能有机分子化学国家重点实验室, 兰州 730000
  • 收稿日期:2007-01-25 修回日期:1900-01-01 出版日期:2007-10-10 发布日期:2007-10-10
  • 通讯作者: 张炜

Synthesis of Quino[1,2-c][1,3]benzoxazin-6-ones by [4+2] Reaction of [1,3]Benzoxazin-2-onium Ions with Olefins

WANG Jun-Pu, ZHANG Wei*, HUANG Li-Min   

  1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2007-01-25 Revised:1900-01-01 Online:2007-10-10 Published:2007-10-10
  • Contact: ZHANG Wei

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摘要： 以BF3·OEt2 为催化剂, 在室温下通过4-羟基-N-苯基[1,3]苯并噁嗪-2-酮的脱羟基产生N-苯基[1,3]苯并噁嗪正离子, 然后与富电子烯烃发生Diels-Alder反应, 合成出了一系列喹啉并[1,2-c][1,3]苯并噁嗪-6-酮和喹啉并[1,2-c][1,3]萘并噁嗪-6-酮衍生物.

关键词: 喹啉并[1,2-c][1,3]苯并噁嗪-6-酮, 4-羟基-N-苯基[1,3]苯并噁嗪-2-酮, N-酰基亚铵离子

Abstract: The N-acyliminium cations are powerful intermediates in the construction of nitrogen-containing heterocycles. They are much more reactive than iminium cations in both intramolecular cyclizations and intermolecular cycloadditions. In this paper, a new and efficient route for the synthesis of quino[1,2-c][1,3]benzoxazin-6-ones (3a—3h) and quino[1,2-c][1,3]naphthoxazin-6-ones (3i—3j) was developed via Diels-Alder reaction of N-acyliminium cations with olefins (2a—2d) in moderate and good yields at an ambient temperature. The N-acyliminium cations, N-phenyl[1,3]benzoxazin-2-onium ion and N-phenyl[1,3]naphthoxazin-2-onium ion, are easily prepared by BF3·OEt2 catalyzed dehydroxylation of 4-hydroxy-3-phenyl[1,3]benzoxazin-2-ones (1a—1c) and 4-hydroxy-3-phenyl[1,3]naphthoxazin-2-one(1d).

Key words: Quino[1,2-c][1,3]benzoxazin-6-one, 4-Hydroxy-N-phenyl[1,3]benzoxazin-2-one, N-acyliminium cation

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