Synthesis of Pharmacologically Relevant Indoles with Amine Side Chains via Tandem Hydroformylation/Fischer Indole Synthesis

2005/06/14 by A. Schmidt, Axel M. Schmidt, Peter Eilbracht · 97 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Amine gas treating #Asymmetric Hydrogenation and Catalysis #Biochemistry #Catalysis #Chemical Synthesis and Analysis #Chemistry #Combinatorial chemistry #Cyclopropane Reaction Mechanisms #Hydroformylation #Indole test #Organic chemistry #Rhodium #Stereochemistry #Tandem #Tryptamine #Tryptamines

paper · doi:10.1021/jo050464l

published in The Journal of Organic Chemistry 70(14), 5528-5535 (American Chemical Society)

openalex publication_date 2005/06/14 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/28

Abstract

[reaction: see text] The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.

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