Tetrahedron p. 9499 - 9508 (1996)
Update date:2022-07-29
Topics:
Cherkaoui, Omar
Nebois, Pascal
Fillion, Houda
Domard, Monique
Fenet, Bernard
Diels-Alder reactions of 5- or 6-bromobenzofuran-4,7-diones 7 or 10 towards azadienes 1 afford regiospecifically furo[2,3] or furo[3,2- g]quinoline-4,9-diones 3 or 4. Assignment of the regioisomers, made by 2D NMR 1H-13C HMBC experiments, showed that the regiochemistry of the cycloadditions is under control of the bromine atom position. Calculations by the semiempirical method PM3 of the HOMO and LUMO orbital coefficients of azadienes 1 and quinones 2 indicated that the larger ones are situated at C- 4 for 1 and C 5 for 2.
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