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Synthesis, proton NMR stereochemical study and diels‐alder reaction of ( E )‐7‐arylidene‐2 H ,6 H ‐naphtho[1,8‐ bc ]furan‐2,6‐diones
Author(s) -
Bouaziz Zouhair,
Fillion Houda,
Pinatel Henri
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300108
Subject(s) - chemistry , furan , diels–alder reaction , medicinal chemistry , proton , stereochemistry , proton nmr , organic chemistry , computational chemistry , catalysis , physics , quantum mechanics
7‐Arylidene‐2 H ,6 H ‐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‐2 H ‐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 1 H 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.