4.7 Article

Transition-metal-free synthesis of 1,4-benzoxazepinesvia[4+3]-cycloaddition ofpara-quinone methides with azaoxyallyl cations

Journal

SCIENCE CHINA-CHEMISTRY
Volume 64, Issue 1, Pages 61-65

Publisher

SCIENCE PRESS
DOI: 10.1007/s11426-020-9832-9

Keywords

1; 4-benzoxazepines; para-quinone methides; azaoxyallyl cations; cycloaddition; transition-metal-free

Funding

  1. National Natural Science Foundation of China [21971001, 21702001]
  2. Natural Science Foundation of Anhui Province [1808085MB47]
  3. Open Fund for Discipline Construction, Institute of Physical Science and Information Technology, Anhui University
  4. Anhui University

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A formal [4+3]-cycloaddition reaction between ortho-hydroxyphenyl-substituted para-quinone methides and in-situ generated azaoxyallyl cations is reported here. This reaction provides a very efficient route to a series of biologically important 1,4-benzoxazepine derivatives in good to excellent yields under mild reaction conditions.
A formal [4+3]-cycloaddition reaction ofortho-hydroxyphenyl-substituted para-quinone methides (p-QMs) within-situgenerated azaoxyallyl cations is reported. The reaction occurs under very mild reaction conditions (transition-metal free, room temperature, cheap inorganic base) and provides a very efficient route to a series of biologically important 1,4-benzoxazepine derivatives in good to excellent yields.

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