220926-62-5Relevant articles and documents
Synthesis of functionalized indole- and benzo-fused heterocyclic derivatives through anionic benzyne cyclization
Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Fernandez, Yolanda
, p. 2034 - 2046 (2007/10/03)
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.
