Synthesis of functionalized indole- and benzo-fused heterocyclic derivatives through anionic benzyne cyclization.
The development of a new method for the regioselective synthesis of functionalized indoles and six-membered benzo-fused N-, O-, and S-heterocycles is reported. The key step involves the generation of a benzyne-tethered vinyl or aryllithium compound that undergoes a subsequent intramolecular anionic cyclization. Reaction of the organolithium intermediates with selected electrophiles allows the preparation of a wide variety of indole, tetrahydrocarbazole, dihydrofenantridine, dibenzopyran, and dibenzothiopyran derivatives. Finally, the application of this strategy to the appropriate starting materials allows the preparation of some tryptamine and serotonin analogues.
Barluenga
José
J
Instituto Universitario de Química Organometálica "Enrique Moles" Unidad Asociada al C.S.I.C. Universidad de Oviedo, Julián Clavería, 8 33071 Oviedo, Spain. barluenga@sauron.quimica.uniovi.es
Fañanás
Francisco J
FJ
Sanz
Roberto
R
Fernández
Yolanda
Y