A novel tandem reaction of 3-substituted coumarins with two equivalents of dimethylsulfoxonium ylide to 2-substituted cyclopenta[ b]benzofuran-3-ol derivatives

When the coumarins ( 4 ) having an electron-withdrawing group at the 3 position were treated with 2.4 equiv. of dimethylsulfoxonium methylide at room temperature in DMF or DMSO, novel tricyclic 2-substituted cyclopenta[ b]benzofuran-3-ols ( 5 ) were obtained in moderate to good yields. The intermedi...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2002-02, Vol.58 (8), p.1497-1505
Main Authors: Yamashita, Masayuki, Okuyama, Kazunori, Kawajiri, Takeshi, Takada, Atsushi, Inagaki, Yumiko, Nakano, Hiromi, Tomiyama, Masataka, Ohnaka, Aya, Terayama, Izumi, Kawasaki, Ikuo, Ohta, Shunsaku
Format: Article
Language:English
Subjects:
benzofurans
coumarins
cyclopropanation
ylides
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:When the coumarins ( 4 ) having an electron-withdrawing group at the 3 position were treated with 2.4 equiv. of dimethylsulfoxonium methylide at room temperature in DMF or DMSO, novel tricyclic 2-substituted cyclopenta[ b]benzofuran-3-ols ( 5 ) were obtained in moderate to good yields. The intermediates, 1a-substituted benzo[ b]cyclopropa[ d]pyran-2(1a H)-ones ( 3 ), of this tandem reaction were isolated and derived to the corresponding 2-substituted cyclopenta[ b]benzofuran-3-ols ( 5 ) by treatment with 1.1 equiv. of dimethylsulfoxonium methylide. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00014-5