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Communication | Special issue | Vol 37, No. 1, 1994, pp.265-274
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S52
Structure and Spectral Properties of β-Carbolines. Part 7. The Pictet-Spengler Reaction of Tryptamines with N-Benzyl-4-piperidone

Maria J. Mokrosz, Piotr Kowalski, Andrzej J. Bojarski, and Jerzy L. Mokrosz*

*Department of Mmedical Chemistry, Institute of Pharmacology, Polish Acadeamy of Sciences, 12 Smetna Street, 31-343 Kraków, Poland

Abstract

The Pictet-Spengler reaction of substituted tryptamines (1b-1g) with N-benzyl-4-piperidone afforded spiro derivatives (3b-3g) with a yield of 11-76%. A charge sensitivity analysis (CSA) of the protonated form of Schiff bases (8) indicated that the intramolecular electrophilic attack at position 3 is favorable in relation to that at position 2.