Synthesis and Diels-Alder reactivity of ortho-carbazolequinones.
Oxidation of 2- and 3-hydroxycarbazoles with Frémy's salt gave the corresponding ortho-carbazolequinones. These molecules react as carbodienophiles in Diels-Alder reaction with 1-acetoxy-1,3-butadiene and 1,3-cyclopentadiene to provide the novel benzocarbazolequinone structures 15, 16, 18 and 19.
Compain-Batissou
Muriel
M
Laboratoire de Chimie Organique, Institut des Sciences Pharmaceutiques et Biologiques, Université Claude Bernard Lyon 1, 69373 Lyon cedex 08, France.
Latreche
Djamila
D
Gentili
Jacques
J
Walchshofer
Nadia
N
Bouaziz
Zouhair
Z
D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry
D002227:Carbazoles; D011809:Quinones