论文信息 - Synthesis, proton NMR stereochemical study and diels-alder reaction of (E)-7-arylidene-2H,6H-naphtho[1,8-bc]furan-2,6-diones

Synthesis, proton NMR stereochemical study and diels-alder reaction of (E)-7-arylidene-2H,6H-naphtho[1,8-bc]furan-2,6-diones

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.

Z. Bouaziz | H. Fillion | H. Pinatel

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