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Communication | Regular issue | Vol 6, No. 8, 1977, pp.1133-1139
Published online, 1st January, 1970
DOI: 10.3987/R-1977-08-1133
Synthesis of 1,2,3,4-Tetrahydro-β-carbolines

Joseph Sandrin, Dave Soerens, Patti Mokry, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.

Abstract

The Pictet-Spengler condensation of acid labile aldehydes with Nb-benzyl tryptophan methyl ester and Nb-benzyl tryptamine has been carried out with carbonyl compounds such as glyoxal diethylacetal and ethyl-3-formylpropionate under non-protic conditions. The condensation in aprotic media does not occur with the free base, tryptamine, but works quite well for Nb-benzyl tryptamine. A study of the influence of various Nb-alkyl groups on the ease of cyclization has been explored. This has resulted in synthesis of β-carbolines, such as 1-salicyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline (5b), which were previously very difficult to prepare.