4.4 Article

Facile synthesis of 3-aryl 2,3-dihydrobenzofurans via novel domino 1,6-addition/O-alkylation reactions of para-quinone methides

Journal

TETRAHEDRON
Volume 74, Issue 13, Pages 1492-1496

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2018.02.008

Keywords

1,6-Addition/O-alkylation; Domino reaction; Ortho-Hydroxyphenylsubstituted p-QMs; Diethyl bromomalonate; 3-Aryl 2,3-dihydrobenzofurans

Funding

  1. National Natural Science Foundation of China [21672031]
  2. Fundamental and Advanced Research Projects of Chongqing City [cstc2016jcyjA0267]
  3. Scientific and Technological Research Program of Chongqing Municipal Education Commission [KJ1600211]

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A facile K2CO3-promoted novel domino 1,6-addition/O-alkylation reaction of ortho-hydroxyphenylsubstituted p-QMs and diethyl bromomalonate is described. A variety of new 3-aryl 2,3-dihydrobenzofurans were obtained in excellent yields (up to 99%) under simple and mild conditions. The structure of the new compound 3f was determined by single crystal X-ray analysis. (C) 2018 Elsevier Ltd. All rights reserved.

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