Z. Bouaziz, H. Fillion, H. Pinatel
1993
Citations
0
Influential Citations
5
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
7-Arylidene-2H,6H-naphtho[1,8-bc]furan-2,6-diones 3 were prepared by a retro-Diels-Alder reaction of the corresponding dihydro 1,3-oxazines 2 or in a one pot synthesis from 6-hydroxy-2H-naphtho[1,8-bc]furan-2-one 1. Their E configuration was established from the chemical shift's values of the vinylic proton and by 1H nmr NOE difference spectroscopy. Cycloadditions of 3b upon styrene or stilbene were catalyzed by boron trifluoride etherate. The cycloadducts were obtained with the relative trans configuration.