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Paper | Special issue | Vol 30, No. 1, 1990, pp.407-414
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S4
Carbon Dioxide: A Reagent for the Simutaneous Protection of Nucleophilic Centers and the Activation of Alternative Locations to Electrophlic Attack. 16. A Novel Synthetic Method for the Side-Chain Functionalization of N-Methyl-o-toluidine and for the Preparation of 2-Substitiuted N-Methylindoles

Alan R. Katritzky,* Wei-Qiang Fan, Kunihiko Akutagawa, and Jin Wang

*Center for Drug Discovery, College of Pharmacy, University of Florida, Gainesville, Florida 32611-7200, U.S.A.

Abstract

N-Methyl-o-toluidine is readily converted into a range of side-chain functionalized derivatives in a one-pot sequence, using carbon dioside for N-protection. The intermediate lithium carbamate is futher lithiated by butyllithium at the side chain methyl group, and then reacted with an electrophile; the product undrergoes acid-catalyzed decarboxylation during work-up. 2-Substituted N-methylindoles are produced when carboxylate esters are used as electrophiles. The yields are good, and no ring-substituted products are detected.