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1-Substituted β-Carbolines by a Pictet−Spengler Cyclization with Thioortho Esters and Carbon−Carbon Bond Formation via N-Sulfonyl Iminium Ions Generated from N,S-Sulfonyl Acetals

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journal contribution
posted on 18.08.2005, 00:00 by Claudio C. Silveira, Luciana A. Felix, Antonio L. Braga, Teodoro S. Kaufman
The reaction of N-tosyltryptamines with thioortho esters, leading to 1-thiosubstituted tetrahydro-β-carbolines under modified Pictet−Spengler conditions, is described. The 1-heterosubstituted β-carbolines furnished 1-substituted β-carbolines upon reaction with Grignard reagents and silyl derivatives under Lewis acid promotion.