A base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins: A simple and direct synthesis of dihydrofurobenzofuran-coumarins

A simple base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins has been reported. A series of polycyclic heterocycles bearing dihydrofurobenzofuran and coumarin blocks were synthesized via Michael/nucleophilic substitution cascade reaction in moderate to exce...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2023-06, Vol.140, p.133487, Article 133487
Main Authors: Du, Si-Si, Zhou, Peng, Mei, Guang-Jian, Jia, Shi-Kun, Hua, Yuan-Zhao, Wang, Min-Can
Format: Article
Language:English
Subjects:
4-hydroxycoumarins
Benzofuro-dihydrofuro-coumarins
chemical reactions
coumarin
crystal structure
Dearomatization annulation
Lewis bases
Polycyclic heterocycles
X-radiation
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A simple base-mediated dearomatization [2 + 3] annulation of 2-nitrobenzofurans with 4-hydroxycoumarins has been reported. A series of polycyclic heterocycles bearing dihydrofurobenzofuran and coumarin blocks were synthesized via Michael/nucleophilic substitution cascade reaction in moderate to excellent yields. 2-Nitrobenzothiophene and 4-hydroxyquinolin-2-one are also tolerated in this protocol. The reaction can be carried out on a gram scale. The configuration of product is confirmed by X-ray single crystal structure analysis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133487