Synthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/Fischer indole synthesis.
[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.
Fachbereich Chemie, Organische Chemie I, Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund.
Axel M
AM
Schmidt
Peter
P
Eilbracht
D000475:Alkenes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D008956:Models, Chemical; D017366:Serotonin Receptor Agonists / Q000138:chemical synthesis* / Q000494:pharmacology; D014363:Tryptamines / Q000138:chemical synthesis*
D000475:Alkenes; D000588:Amines; D006834:Hydrazines; D007211:Indoles; D017366:Serotonin Receptor Agonists; D014363:Tryptamines