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DOI: 10.1055/s-0036-1588934
Mannich N-Indolylmethylation of Amino Acids
Publication History
Received: 20 October 2016
Accepted after revision: 20 December 2016
Publication Date:
31 January 2017 (online)
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Abstract
Unprotected amino acids and simple peptides (2 examples) with free amino groups are N-indol-3-ylmethylated by a combination of paraformaldehyde or formalin and indole in aqueous ethanol at temperatures from 55–75 °C. Secondary amine incorporating amino acids and primary amine functionalized α-branched amino acids give rise to N-monoalkylation products, whereas unbranched primary amine functionalized amino acids and alanine give N,N-dialkylated products. The modified amino acids are amenable to amide coupling. Other electron-rich (hetero)aromatic cores besides indole (pyrrole, naphthol) are also selectively aminomethylated by amino acids and formaldehyde.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588934.
- Supporting Information
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