A new approach to fused furan ring systems and benzofurans: intramolecular cyclization reactions of unsaturated acyloxy sulfone derivatives

A new strategy for the preparation of fused furan rings and benzofurans via intramolecular cyclization of acyloxy sulfones is described. Unsaturated acyloxy sulfones 3 undergo intramolecular cyclization upon deprotonation with LHMDS in THF. Dehydration and double bond isomerization of the products u...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron letters 2011-06, Vol.52 (23), p.2935-2939
Main Authors: Liu, Yuan, Jacobs, Hollie K., Gopalan, Aravamudan S.
Format: Article
Language:English
Subjects:
Acyloxy sulfone
Annulation
Benzofurans
Bonding
Chemistry
Derivatives
Exact sciences and technology
Furans
Fused furan rings
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Intramolecular cyclization
Isomerization
Noncondensed benzenic compounds
Organic chemistry
Phenols
Preparations and properties
Strategy
Sulfones
Unsaturated
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:A new strategy for the preparation of fused furan rings and benzofurans via intramolecular cyclization of acyloxy sulfones is described. Unsaturated acyloxy sulfones 3 undergo intramolecular cyclization upon deprotonation with LHMDS in THF. Dehydration and double bond isomerization of the products upon exposure to acid, gave the fused ring furans, 4, in good yields. This strategy could be readily adapted to prepare substituted benzofurans 12 from the cyclization reactions of acyloxy sulfones 11 prepared from phenols. Finally, this approach could be successfully modified to access dihydropyrans and benzopyrans.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.03.120