Synthesis of Functionalized Indole??and Benzo??Fused Heterocyclic Derivatives through Anionic Benzyne Cyclization

J Barluenga, FJ Fananas, R Sanz…

Index: Barluenga, Jose; Fananas, Francisco J.; Sanz, Roberto; Fernandez, Yolanda Chemistry - A European Journal, 2002 , vol. 8, # 9 p. 2034 - 2046

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Citation Number: 76

Abstract

Abstract 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 ...