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Diels-alder reactions with ethyl 1-benzofuran-3-carboxylates

Authors :
Tatyana V. Rybalova
Elvira E. Shults
A. S. Kil’met’ev
Makhmut M. Shakirov
Tolstikov Genrikh A
Source :
Russian Journal of Organic Chemistry. 49:872-885
Publication Year :
2013
Publisher :
Pleiades Publishing Ltd, 2013.

Abstract

Substituted salicylaldehydes reacted with ethyl diazoacetate to give ethyl 1-benzofuran-3-carboxylates containing various substituents in the aromatic ring. The Diels-Alder reaction of these compounds with Danishefsky’s diene was regioselective, and it provided an effective method for the construction of the heterocyclic skeleton of hexahydrodibenzo[b,d]furan-7-one or tetrahydrodibenzo[b,d]furan-7-one. The adducts were found to undergo rearrangement to substituted 4′-hydroxybiphenyl-2-yl methyl carbonates during column chromatography on silica gel.

Details

ISSN :
16083393 and 10704280
Volume :
49
Database :
OpenAIRE
Journal :
Russian Journal of Organic Chemistry
Accession number :
edsair.doi...........f4c4022dc77d006a8e16e809563f4633