Synthesis of new 2-vinylation products of indole via a Michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles.
Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles. Diels-Alder reactions of the 2-vinylindoles with naphthoquinone, p-benzoquinone, 1,2-dicyano-4,5-dichloroquinone, N-phenyltriazolinedione, and tetracyanoethylene were investigated to give [c]annelated 1,2-dihydro, 1,2,3,4-tetrahydro, and fully aromatized carbazoles. The structure and formation mechanism of both 2-vinylindoles and their cycloadduct are discussed.
Cavdar
Hüseyin
H
Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey.
Saraçoglu
Nurullah
N
D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D002227:Carbazoles; D002264:Carboxylic Acids; D007211:Indoles; D014753:Vinyl Compounds